subject:(Chemistry Organic)

1. Jayasekara, Himali Devika. Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures.

Degree: 2014, Marquette University

URL: https://epublications.marquette.edu/theses_open/247

► Cage compounds have become an important tool for the study of biological processes. The research focuses on new cage compounds that can unmask functional groups… (more)

▼ Cage compounds have become an important tool for the study of biological processes. The research focuses on new cage compounds that can unmask functional groups present in biologically important molecules such as proteins, peptides, and oligonucleosides. The project focuses on certain functional groups that are often difficult to release photochemically. These are the thiolate groups present in cysteine residues of proteins and peptides. Thiolate groups are fairly basic leaving groups, unlike the more labile groups such as the carboxylates that are present in proteins and peptides, or the phosphate groups present in nucleosides. The research takes advantage of the ability of zwitterionic intermediates to release basic leaving groups such as the thiolates. The zwitterionic intermediates are generated photochemically by electrocyclic ring closure of aromatic carboxamides that has the chromophore attached to the amide nitrogen. Most importantly, the research utilizes a chromophore that absorbs visible light, so as to minimize the damaging effects that short-wavelength light has on tissue and cells. The research recognizes that triplet energy transfer from triplet excited state of the chromophore to the aromatic ring system attached to carboxamide carbonyl group must be exothermic in order for the electrocyclic ring closure to occur. For a thioxanthone chromophore (ET = 64 kcal mol-1), the aromatic ring system is a naphthothiophene ring system (ET = 62 kcal mol-1). The energy transfer would therefore be exothermic. This cage compound was synthesized with a 3-chloro leaving group. It undergoes photochemical electrocyclic ring closure and chloride expulsion in 50% yield after 1.5 h photolysis. The reaction qualitatively appears to be efficient. In comparison, a 5-benzoylthiophene aromatic ring system with 3-chloro group undergoes the same photoreaction in very low yields over 72 h, even though the triplet energy transfer is exothermic. In this case the photoproduct effectively competes for the incident light with the reactant. The research shows that the naphthothiophene ring system is a viable solution to the triplet energy transfer problem. It also points to a need to improve the solubility of the cage compound by incorporating one or more carboxylate groups into the naphthothiophene ring or the thioxanthone ring. Advisors/Committee Members: Steinmetz, Mark G., Donaldson, William A., Timerghazin, Qadir K..

Subjects/Keywords: Organic chemistry; Chemistry; Organic Chemistry

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APA (6^th Edition):

Jayasekara, H. D. (2014). Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures. (Thesis). Marquette University. Retrieved from https://epublications.marquette.edu/theses_open/247

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Jayasekara, Himali Devika. “Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures.” 2014. Thesis, Marquette University. Accessed September 19, 2019. https://epublications.marquette.edu/theses_open/247.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Jayasekara, Himali Devika. “Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures.” 2014. Web. 19 Sep 2019.

Vancouver:

Jayasekara HD. Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures. [Internet] [Thesis]. Marquette University; 2014. [cited 2019 Sep 19]. Available from: https://epublications.marquette.edu/theses_open/247.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Jayasekara HD. Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures. [Thesis]. Marquette University; 2014. Available from: https://epublications.marquette.edu/theses_open/247

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Iowa State University

2. Drochner, Dana Lynn. Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials.

Degree: 2015, Iowa State University

URL: https://lib.dr.iastate.edu/etd/14793

► This research explores the synthesis and evaluation of new building blocks and polymers for organic photovoltaic materials. Through the development of new synthetic routes and… (more)

Subjects/Keywords: Organic Chemistry; Chemistry; Organic Chemistry

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APA (6^th Edition):

Drochner, D. L. (2015). Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials. (Thesis). Iowa State University. Retrieved from https://lib.dr.iastate.edu/etd/14793

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Drochner, Dana Lynn. “Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials.” 2015. Thesis, Iowa State University. Accessed September 19, 2019. https://lib.dr.iastate.edu/etd/14793.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Drochner, Dana Lynn. “Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials.” 2015. Web. 19 Sep 2019.

Vancouver:

Drochner DL. Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials. [Internet] [Thesis]. Iowa State University; 2015. [cited 2019 Sep 19]. Available from: https://lib.dr.iastate.edu/etd/14793.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Drochner DL. Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials. [Thesis]. Iowa State University; 2015. Available from: https://lib.dr.iastate.edu/etd/14793

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Oxford

3. Liddon, John Timothy Ruskin. The versatile chemistry of azidoalkyl enol ethers and their equivalents.

Degree: PhD, 2015, University of Oxford

URL: http://ora.ox.ac.uk/objects/uuid:a5554d44-d251-4ca5-8b2d-d07a7c95138a ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.664830

► This thesis describes the synthesis and intramolecular cycloaddition products of azides tethered to olefins bearing a heteroatom in an attempt to access a proposed triazolium… (more)

Subjects/Keywords: 547; Chemistry; Organic Chemistry; Organic

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APA (6^th Edition):

Liddon, J. T. R. (2015). The versatile chemistry of azidoalkyl enol ethers and their equivalents. (Doctoral Dissertation). University of Oxford. Retrieved from http://ora.ox.ac.uk/objects/uuid:a5554d44-d251-4ca5-8b2d-d07a7c95138a ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.664830

Chicago Manual of Style (16^th Edition):

Liddon, John Timothy Ruskin. “The versatile chemistry of azidoalkyl enol ethers and their equivalents.” 2015. Doctoral Dissertation, University of Oxford. Accessed September 19, 2019. http://ora.ox.ac.uk/objects/uuid:a5554d44-d251-4ca5-8b2d-d07a7c95138a ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.664830.

MLA Handbook (7^th Edition):

Liddon, John Timothy Ruskin. “The versatile chemistry of azidoalkyl enol ethers and their equivalents.” 2015. Web. 19 Sep 2019.

Vancouver:

Liddon JTR. The versatile chemistry of azidoalkyl enol ethers and their equivalents. [Internet] [Doctoral dissertation]. University of Oxford; 2015. [cited 2019 Sep 19]. Available from: http://ora.ox.ac.uk/objects/uuid:a5554d44-d251-4ca5-8b2d-d07a7c95138a ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.664830.

Council of Science Editors:

Liddon JTR. The versatile chemistry of azidoalkyl enol ethers and their equivalents. [Doctoral Dissertation]. University of Oxford; 2015. Available from: http://ora.ox.ac.uk/objects/uuid:a5554d44-d251-4ca5-8b2d-d07a7c95138a ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.664830

University of Helsinki

4. Raffaelli, Barbara. Synthesis of lignano-9,9'-lactones and rearrangement studies.

Degree: Department of Chemistry, Laboratory of Organic Chemistry, 2012, University of Helsinki

URL: http://hdl.handle.net/10138/37066

►

Lignans are found as naturally occurring compounds in plants, and also as metabolites in mammals. Due to their biological activity, lignans have attracted the interest… (more)

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Lignans are found as naturally occurring compounds in plants, and also as metabolites in mammals. Due to their biological activity, lignans have attracted the interest of scientists from different areas like food chemistry, synthetic chemistry, and clinical chemistry. The research is very active, as evident by the number of publications related to this subject that are published annually. The present work focuses on the chemistry of certain classes of lignan, namely lignano-9,9'-lactones and their rearranged products. The literature review is based on the synthesis of lignano-9,9'-lactones and 7'-OH-lignano-9,9'-lactones. Both racemic and asymmetric protocols appeared as from year 2000 have been extensively reviewed. In addition, the literature concerning the rearrangement reaction of 7'-OH-lignano-9,9'-lactones have been discussed. The experimental section presents the development of a stereoselective synthesis to obtain 7'-hydroxylignanolactones. Subsequently, the known rearrangement reactions affecting hydroxylignanolactones are discussed. The stereochemistry of certain lignanolactones is a core part of this work and the findings of this study allowed the revision of certain controversial data found in the literature. For the first time, the X-ray structures of 7'-OH-lignano-9,9'-lactones were obtained. In addition, the synthesis of possible lignan metabolites is also presented. A summary of the available 1H NMR data for selected (7'S)- and (7'R)-OH-lignano-9,9'-lactones and for various lignano-9,7'-lactone stereoisomers has been made available in the Appendix section.

Lignaanit ovat mielenkiintoinen ihmisen terveyteen vaikuttavien aineiden ryhmä, joita esiintyy luonnossa kasveissa, erityisesti hedelmissä ja vihanneksissa. Lignaaneihin kohdistuva tieteellinen mielenkiinto johtuu niiden moninaisista rakennevariaatioista, ja ennen kaikkea niiden monista biologisista vaikutuksista. Lignaanien perusrakenne koostuu kahdesta fenyylipropaaniyksiköstä, jotka ovat sitoutuneet toisiinsa C-C -sidoksella propaaniyksikköjen keskihiilien kautta. Rakenteellista monimuotoisuutta aiheuttavat muut C-C sidokset, hapetusasteen vaihtelut, ja sekä alifaattisiin että aromaattisiin hiiliatomeihin kiinnittyneet erilaiset substituentit. Kasvikunta käyttää lignaaneja sienten ja hyönteisten torjuntaan. Ajankohtaisempaa on lignaanien merkitys liittyen ihmisen terveyteen. Kirjallisuudessa on raportoitu syövän vastaisista, antioksidatiivisista, anti-inflammatorisista ja apoptoottisista vaikutuksista sekä virusten torjunnasta. Suurta mielenkiintoa ovat herättäneet ihmisistä löytyneet lignaanit, jotka ovat muodostuneet elimistön aineenvaihdunnan tuloksena ravinnon mukana nautituista kasvilignaanerista. Näillä uusilla enterolignaaneilla on havaittu suojaavaa vaikutusta moninaisia terveyden haittatiloja kohtaan, kuten eturauhas-, rinta-, suoli- ja muut syövät, sydän- ja verisuonitaudit, aivotaudit, menopaussioireet ja osteoporoosi. Enterolignaanien rakenne muistuttaa endogeenisen 17beta-estradiolihormonin rakennetta, ja enterolignaanien…

Subjects/Keywords: organic Chemistry; organic Chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Raffaelli, B. (2012). Synthesis of lignano-9,9'-lactones and rearrangement studies. (Doctoral Dissertation). University of Helsinki. Retrieved from http://hdl.handle.net/10138/37066

Chicago Manual of Style (16^th Edition):

Raffaelli, Barbara. “Synthesis of lignano-9,9'-lactones and rearrangement studies.” 2012. Doctoral Dissertation, University of Helsinki. Accessed September 19, 2019. http://hdl.handle.net/10138/37066.

MLA Handbook (7^th Edition):

Raffaelli, Barbara. “Synthesis of lignano-9,9'-lactones and rearrangement studies.” 2012. Web. 19 Sep 2019.

Vancouver:

Raffaelli B. Synthesis of lignano-9,9'-lactones and rearrangement studies. [Internet] [Doctoral dissertation]. University of Helsinki; 2012. [cited 2019 Sep 19]. Available from: http://hdl.handle.net/10138/37066.

Council of Science Editors:

Raffaelli B. Synthesis of lignano-9,9'-lactones and rearrangement studies. [Doctoral Dissertation]. University of Helsinki; 2012. Available from: http://hdl.handle.net/10138/37066

5. Lee, Jennifer Jiyoung. Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy.

Degree: 2014, Iowa State University

URL: https://lib.dr.iastate.edu/etd/14190

► The chemical industry relies on crude oil to manufacture the vast majority of chemicals. However, the increasing demand cannot be supported with the simultaneous decrease… (more)

▼ The chemical industry relies on crude oil to manufacture the vast majority of chemicals. However, the increasing demand cannot be supported with the simultaneous decrease in natural crude oil reserves and increasing prices. Green chemistry solutions may resolve the issue utilizing biorenewable feedstocks, especially for the functionalized aromatic compounds that are ubiquitous in a wide variety of consumer materials. The atom economical Diels-Alder reaction installs two carbon-carbon bonds with high levels of regio-, chemo-, and stereocontrol, which was effectively utilized in a platform approach. Through metabolic engineering, glucose can be converted to malic acid. Afterwards, dimerization and esterification provided the 2-pyrone methyl coumalate as a platform molecule for the methodology. Although unactivated alkenes resulted in aromatic compounds, palladium was required, and with electron-deficient alkene dienophiles, mixtures of regioisomers were observed. In contrast, we developed an inverse electron-demand Diels-Alder/retro-Diels-Alder/elimination domino methodology from methyl coumalate with electron-rich olefins to regioselectively furnish diverse aromatic compounds. Vinyl ether dienophiles provided a broad range of aromatic compounds, which were equipped with an alkoxy leaving group to facilitate aromatization without a catalyst. The scope was expanded with readily prepared acetal and orthoester dienophile equivalents that could be utilized in crude form. As practical bench-stable compounds, elimination occurred under the thermal conditions to reveal the dienophile. The metal-free, one-pot domino sequence efficiently provided high yields and regioselectivities for the desired aromatic compounds. The expansive range of accessible aromatic compounds through the methodology included carbazoles, tricyclic, fused, anisole, and biphenyl systems. Notably, captodative dienophile derivatives from methyl pyruvate provided a 100% biorenewable formal synthesis to terephthalic acid with dimethyl terephthalate as the intermediate. As commodity co-monomers for poly(ethylene terephthalate), the green methodology was further optimized to remove the reaction solvent and recrystallize the product in up to 95% yield. In summary, methyl coumalate represents a convenient bio-based platform for diverse aromatics which fulfills many green chemistry principles in the progress toward a sustainable future.

Subjects/Keywords: Organic Chemistry; Organic Chemistry

3 more images…

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APA (6^th Edition):

Lee, J. J. (2014). Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy. (Thesis). Iowa State University. Retrieved from https://lib.dr.iastate.edu/etd/14190

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Lee, Jennifer Jiyoung. “Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy.” 2014. Thesis, Iowa State University. Accessed September 19, 2019. https://lib.dr.iastate.edu/etd/14190.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Lee, Jennifer Jiyoung. “Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy.” 2014. Web. 19 Sep 2019.

Vancouver:

Lee JJ. Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy. [Internet] [Thesis]. Iowa State University; 2014. [cited 2019 Sep 19]. Available from: https://lib.dr.iastate.edu/etd/14190.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Lee JJ. Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy. [Thesis]. Iowa State University; 2014. Available from: https://lib.dr.iastate.edu/etd/14190

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

McMaster University

6. Jeyakanthan, Ketharagowry. A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES.

Degree: MSc, 2014, McMaster University

URL: http://hdl.handle.net/11375/14137

►

Three novel 1-aryl-1-(3-butenyl)germacyclopent-3-enes (26a, 26b and 26c) were synthesized and their photochemistry in hexane solution was studied by steady state and laser flash photolysis… (more)

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Three novel 1-aryl-1-(3-butenyl)germacyclopent-3-enes (26a, 26b and 26c) were synthesized and their photochemistry in hexane solution was studied by steady state and laser flash photolysis (LFP) methods. Steady state photolysis of 1-(3-butenyl)-3,4-dimethyl-1-phenylgermacyclopent-3- ene (26a) was found to proceed cleanly to afford the corresponding germylene derived product along with 2,3-dimethyl-1,3-butadiene (DMB) in the presence of acetic acid, methanol and isoprene, suggesting that free (3-butenyl)phenylgermylene (GeBuPh) is the primary photochemically generated species. However, we were unable to detect the germylene by laser flash photolysis with this compound, due to rapid “self –quenching” of the germylene by the precursor. The direct detection of the germylene in solution by laser flash photolysis requires the use of a more strongly absorbing derivative. Indeed, 3-butenylphenylgermylene (GeBuPh) was successfully detected directly by laser flash photolysis of 1-(3-butenyl)-3-methyl-1,4-diphenylgermacyclopent-3-ene (26b) in hexane solution, where it exhibits a UV-Vis absorption band centered at λmax= 490 nm and decays with second order kinetics on the microsecond timescale. In the absence of reactive substrates the decay of GeBuPh is accompanied by the growth of a second transient absorption, assigned to Ge2Bu2Ph2 (34) λmax = 420 nm; the assignment is based on a comparison to the laser flash photolysis of 1,3-dimethyl-1,4- diphenylgermacyclopent-3-ene (26d). Rate constants have been determined for reaction iv of the germylene with selected germylene substrates in order to evaluate the effects of intramolecular π-complexation on its reactivity. The results indicate that GeBuPh exhibits similar reactivity to GeMePh under otherwise identical experimental conditions, and thus show no significant indication of intramolecular π-complexation. With this in mind we have synthesized and studied 1-(3-butenyl)-3-methyl-4- phenyl-1-[3,5-bis(trifluoromethyl)phenyl]germacyclopent-3-ene (26c), which was designed to produce a more strongly electrophilic Ge(II) center in the corresponding germylene. The germylene 46 is detectable as a weakly absorbing transient species with λmax = 490 nm by laser flash photolysis of 26c in hexane solution. Generation of germylene 46 in the presence of THF leads to the formation of the corresponding Lewis acid base complex 48 at λmax = 330 nm. The reactivity of germylene 46 with selected substrates such as AcOH, THF and isoprene has been examined and the results compared to analogous data for the parent germylene GeBuPh. The forward rate constant for germylene 46 with acetic acid is slightly higher than that for GeBuPh, and no evidence for intramolecular complexation with the remote C=C bond could be obtained.

Master of Science (MSc)

Advisors/Committee Members: J.Leigh, William, Vargas-Baca, Ignacio, Chemistry and Chemical Biology.

Subjects/Keywords: Organic Chemistry; Organic Chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Jeyakanthan, K. (2014). A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES. (Masters Thesis). McMaster University. Retrieved from http://hdl.handle.net/11375/14137

Chicago Manual of Style (16^th Edition):

Jeyakanthan, Ketharagowry. “A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES.” 2014. Masters Thesis, McMaster University. Accessed September 19, 2019. http://hdl.handle.net/11375/14137.

MLA Handbook (7^th Edition):

Jeyakanthan, Ketharagowry. “A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES.” 2014. Web. 19 Sep 2019.

Vancouver:

Jeyakanthan K. A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES. [Internet] [Masters thesis]. McMaster University; 2014. [cited 2019 Sep 19]. Available from: http://hdl.handle.net/11375/14137.

Council of Science Editors:

Jeyakanthan K. A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES. [Masters Thesis]. McMaster University; 2014. Available from: http://hdl.handle.net/11375/14137

Iowa State University

7. Goswami, Pratik Pran. Development of light- and chemo-sensitive probes for biochemical methods.

Degree: 2015, Iowa State University

URL: https://lib.dr.iastate.edu/etd/14369

► Part I. Photocages, which are light cleavable protecting groups, are an important class of chemical tools that allow light to unmask bioactive substrates with precise… (more)

▼ Part I. Photocages, which are light cleavable protecting groups, are an important class of chemical tools that allow light to unmask bioactive substrates with precise spatiotemporal resolution in biological microenvironments. Due to their effectiveness in biological systems, it has become increasingly important to find logically designed photocages that can cleave under visible light and Near IR conditions, wavelengths with minimal phototoxicity and increased tissue penetration compared to ultraviolet light. The scope of this research is to both rationally design and synthesize a new class of photocage based on the BODIPY moiety, as well as to modify these photocages to absorb in region of the biological window (600-1000 nm), where tissues have maximal transparency. In chapter 1, photocages derived from meso-substituted BODIPY dyes were synthesized that release acetic acid when irradiated with green wavelengths (>500 nm). The structures of the photocages were derived by computationally searching for carbocations with low-energy diradical states as a possible indicator of nearby productive conical intersections. These photocages were found to have superior optical properties than the popular o-nitrobenzyl systems, which make them promising alternatives. The utility of these photocages in living cells was successfully demonstrated by our collaborators (Prof. Emily Smith and Aleem Syed) in cultured S2 cells. In Chapter 2, Knoevenagel type reactions were used to extend the π electron conjugation of the aromatic rings of the BODIPY photocages. This extended conjugation of these BODIPY photocages resulted in a bathochromic shift in absorbance towards red light (>600 nm) and allows cleavage using wavelengths in the biological window. Part II. Self-immolative linkers can be used to trigger the release of an important cargo molecule like a drug or a biomolecule. A variety of trigger stimulants including light, chemo and enzyme are known in literature. However, there is a need for new linker units which would have fast and controllable kinetics of cargo release. During my research, I identified improved self-immolative linker units based on aryl phthalate esters with a modular design, which can tolerate a range of different trigger and cargo units. In Chapter 3, new types of self-immolative linkers based on the phenyl hydrogen phthalate system were synthesized. The fast kinetic rate for the hydrolysis of phenyl hydrogen phthalate system and the resulting benign byproducts promise a robust self-immolative linker system that can be used in biological systems. The linker system was shown to release phenol based cargo molecules including phenol and coumarin dyes upon cleavage by a fluoride sensitive trigger. This type of linker can also be potentially used as an efficient fluoride sensor. In Chapter 4, the scope of self-immolative linkers based on phenyl hydrogen phthalate system was extended. Light and peroxide sensitive triggers were incorporated into the linker system. Coumarin based cargo molecules were used as reporter…

Subjects/Keywords: Organic Chemistry; Organic Chemistry

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APA (6^th Edition):

Goswami, P. P. (2015). Development of light- and chemo-sensitive probes for biochemical methods. (Thesis). Iowa State University. Retrieved from https://lib.dr.iastate.edu/etd/14369

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Goswami, Pratik Pran. “Development of light- and chemo-sensitive probes for biochemical methods.” 2015. Thesis, Iowa State University. Accessed September 19, 2019. https://lib.dr.iastate.edu/etd/14369.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Goswami, Pratik Pran. “Development of light- and chemo-sensitive probes for biochemical methods.” 2015. Web. 19 Sep 2019.

Vancouver:

Goswami PP. Development of light- and chemo-sensitive probes for biochemical methods. [Internet] [Thesis]. Iowa State University; 2015. [cited 2019 Sep 19]. Available from: https://lib.dr.iastate.edu/etd/14369.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Goswami PP. Development of light- and chemo-sensitive probes for biochemical methods. [Thesis]. Iowa State University; 2015. Available from: https://lib.dr.iastate.edu/etd/14369

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Iowa State University

8. Bhuwalka, Achala. Design and synthesis of novel heterocycles for organic semiconducting materials.

Degree: 2014, Iowa State University

URL: https://lib.dr.iastate.edu/etd/14123

► Organic semiconductors have attracted much attention as alternatives to silicon based photovoltaic technology. Currently, the best power conversion efficiencies use small molecules and conjugated polymers… (more)

Subjects/Keywords: Organic Chemistry; Organic Chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Bhuwalka, A. (2014). Design and synthesis of novel heterocycles for organic semiconducting materials. (Thesis). Iowa State University. Retrieved from https://lib.dr.iastate.edu/etd/14123

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Bhuwalka, Achala. “Design and synthesis of novel heterocycles for organic semiconducting materials.” 2014. Thesis, Iowa State University. Accessed September 19, 2019. https://lib.dr.iastate.edu/etd/14123.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Bhuwalka, Achala. “Design and synthesis of novel heterocycles for organic semiconducting materials.” 2014. Web. 19 Sep 2019.

Vancouver:

Bhuwalka A. Design and synthesis of novel heterocycles for organic semiconducting materials. [Internet] [Thesis]. Iowa State University; 2014. [cited 2019 Sep 19]. Available from: https://lib.dr.iastate.edu/etd/14123.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Bhuwalka A. Design and synthesis of novel heterocycles for organic semiconducting materials. [Thesis]. Iowa State University; 2014. Available from: https://lib.dr.iastate.edu/etd/14123

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Wright State University

9. Boyer, Amanda Merrill. Potential Tau Directed Imaging Agents.

Degree: MS, Chemistry, 2015, Wright State University

URL: http://rave.ohiolink.edu/etdc/view?acc_num=wright1453210267

► Given the ambident reactivity of oxindoles in terms of N- versus C-alkylation, realization of the three points of diversity available to (presumably benzenoid substituted) benzylidene… (more)

Subjects/Keywords: Chemistry; Organic Chemistry; chemistry; organic chemistry

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APA (6^th Edition):

Boyer, A. M. (2015). Potential Tau Directed Imaging Agents. (Masters Thesis). Wright State University. Retrieved from http://rave.ohiolink.edu/etdc/view?acc_num=wright1453210267

Chicago Manual of Style (16^th Edition):

Boyer, Amanda Merrill. “Potential Tau Directed Imaging Agents.” 2015. Masters Thesis, Wright State University. Accessed September 19, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=wright1453210267.

MLA Handbook (7^th Edition):

Boyer, Amanda Merrill. “Potential Tau Directed Imaging Agents.” 2015. Web. 19 Sep 2019.

Vancouver:

Boyer AM. Potential Tau Directed Imaging Agents. [Internet] [Masters thesis]. Wright State University; 2015. [cited 2019 Sep 19]. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=wright1453210267.

Council of Science Editors:

Boyer AM. Potential Tau Directed Imaging Agents. [Masters Thesis]. Wright State University; 2015. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=wright1453210267

10. Omran, Anahid. Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands.

Degree: 2017, Southern Illinois University at Edwardsville

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=10616167

► Dysfunction of dopaminergic receptor signaling in the brain is a hallmark of a number of neurodegenerative pathologies. Of the five dopamine receptors, the D₃… (more)

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

Omran, A. (2017). Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands. (Thesis). Southern Illinois University at Edwardsville. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=10616167

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Omran, Anahid. “Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands.” 2017. Thesis, Southern Illinois University at Edwardsville. Accessed September 19, 2019. http://pqdtopen.proquest.com/#viewpdf?dispub=10616167.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Omran, Anahid. “Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands.” 2017. Web. 19 Sep 2019.

Vancouver:

Omran A. Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands. [Internet] [Thesis]. Southern Illinois University at Edwardsville; 2017. [cited 2019 Sep 19]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10616167.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Omran A. Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands. [Thesis]. Southern Illinois University at Edwardsville; 2017. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10616167

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Temple University

11. GADDIRAJU, NARENDRA VARMA. Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters.

Degree: PhD, 2013, Temple University

URL: http://digital.library.temple.edu/u?/p245801coll10,225834

►

Chemistry

Organic nitrogen containing chiral compounds are widely found in nature, and a number of them exhibit important biological and medicinal properties. The main objective… (more)

▼

Chemistry

Organic nitrogen containing chiral compounds are widely found in nature, and a number of them exhibit important biological and medicinal properties. The main objective of this research is to develop new methods for the asymmetric synthesis of cocaine analogues having methyl (Me), ethyl (Et), n-propyl (n-Pr), n-pentyl (n-C5H11) and phenyl (Ph) groups at the C-1 bridgehead position. The second project concerned the asymmetric synthesis of anti-α-alkyl substituted beta-amino esters, a new chiral building block, utilizing chiral sulfinimine (N-sulfinyl imine) chemistry. The easy availability and abuse of (R)-(-)-cocaine is a global problem and has resulted in many efforts aimed at the preparation of therapeutically useful cocaine analogues. However, to date analogues of cocaine for the treatment of cocaine addiction have not been reported. The requirement of a cis relationship between C-2 and C-3 substituents in the cocaine tropane skeleton where C-2 carbomethoxy group occupies the thermodynamically unfavorable axial position is the main reason for the difficulty in designing efficient asymmetric syntheses of cocaine analogues. In this study, diastereomerically pure N-sulfinyl beta-amino esters were prepared by the addition of the sodium enolate of methyl acetate to masked oxo sulfinimines, novel sulfinimines having a protected carbonyl group. Reduction of the beta-amino esters gave the corresponding beta-amino aldehydes and a Roush-Masamune modified Horner-Wadsworth-Emmons (HWE) reaction afforded the trans-N-sulfinyl alpha,beta-unsaturated delta-amino esters in good yield. Acid hydrolysis of the esters unmasked the carbonyl group and deprotected the amines resulting in an intramolecular cyclization to produce the key dehydropyrrolidines. Regioselective oxidation of the dehydropyrrolidines using catalytic methyl trioxorhenium and urea-hydrogen peroxide gave the corresponding pyrrolidine nitrones in excellent yield. On heating with the Lewis acid catalyst Al(O-t-Bu)3 the nitrones underwent a novel, stereospecific, intramolecular [3+2] cycloaddition reaction to give tricyclic isoxazolidines. Importantly, the isoxazolidine establishes the necessary cis relationship between C-2 and C-3 substituents in cocaine skeleton. The tricyclic isoxazolidines were readily converted to the N-Me quaternary ammonium salts on heating with methylmethanesulfonate and hydrogenolysis with Pd/C at 1 atm of H2 cleave the N-O bond to afford the ecgonine methyl ester, the tropane alcohol. In contrast to other C-3 (R = Me, Et, n-Pr, Ph) isoxazolidine quaternary ammonium salts, the C-3 n-C5H11 analogue did not undergo N-O bond cleavage under the hydrogenolysis conditions. This analogue rearrange to a bridged bicyclic [4.2.1]isoxazolidine. It was found that all C-3 isoxazolidine N-Me quaternary ammonium salts undergo this rearrangement on treatment with triethylamine. Fortunately, hydrogenolysis of n-C5H11 isoxazolidine quaternary ammonium salt at 4 atm of H2 cleaved the N-O bond to give the desired alcohol, ecgonine methyl ester.…

Advisors/Committee Members: Davis, Franklin A.;, Andrade, Rodrigo B., Wuest, William M., Cannon, Kevin C.;.

Subjects/Keywords: Chemistry; Organic chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

GADDIRAJU, N. V. (2013). Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters. (Doctoral Dissertation). Temple University. Retrieved from http://digital.library.temple.edu/u?/p245801coll10,225834

Chicago Manual of Style (16^th Edition):

GADDIRAJU, NARENDRA VARMA. “Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters.” 2013. Doctoral Dissertation, Temple University. Accessed September 19, 2019. http://digital.library.temple.edu/u?/p245801coll10,225834.

MLA Handbook (7^th Edition):

GADDIRAJU, NARENDRA VARMA. “Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters.” 2013. Web. 19 Sep 2019.

Vancouver:

GADDIRAJU NV. Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters. [Internet] [Doctoral dissertation]. Temple University; 2013. [cited 2019 Sep 19]. Available from: http://digital.library.temple.edu/u?/p245801coll10,225834.

Council of Science Editors:

GADDIRAJU NV. Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters. [Doctoral Dissertation]. Temple University; 2013. Available from: http://digital.library.temple.edu/u?/p245801coll10,225834

12. Guerrera, Cessandra. Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction.

Degree: 2017, Southern Connecticut State University

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=10283110

► Arginase is a manganese-containing enzyme that catalyzes the hydrolysis of L-arginine to yield L-ornithine and urea. It has been suggested that inhibition of arginase… (more)

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

Guerrera, C. (2017). Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction. (Thesis). Southern Connecticut State University. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=10283110

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Guerrera, Cessandra. “Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction.” 2017. Thesis, Southern Connecticut State University. Accessed September 19, 2019. http://pqdtopen.proquest.com/#viewpdf?dispub=10283110.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Guerrera, Cessandra. “Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction.” 2017. Web. 19 Sep 2019.

Vancouver:

Guerrera C. Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction. [Internet] [Thesis]. Southern Connecticut State University; 2017. [cited 2019 Sep 19]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10283110.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Guerrera C. Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction. [Thesis]. Southern Connecticut State University; 2017. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10283110

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Vermont

13. Machamer, Natalie Kay. I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis.

Degree: PhD, Chemistry, 2015, University of Vermont

URL: https://scholarworks.uvm.edu/graddis/407

► Nitrogen-containing heterocycles have great utility in the biomedical and medicinal fields and one such heterocycle is the 5-membered pyrrolidine ring. The synthesis of pyrrolidine… (more)

▼ Nitrogen-containing heterocycles have great utility in the biomedical and medicinal fields and one such heterocycle is the 5-membered pyrrolidine ring. The synthesis of pyrrolidine rings has been studied extensively with the routes relying on anodic oxidation, transition metals and dipolar cycloadditions with azomethine ylides. Previous work in the Waters group has been focused on new routes to azomethine ylides through a domino sequence. Through a thermal aza-Cope rearrangement followed by [3+2] dipolar cycloaddition the synthesis of a library of 2-allyl pyrrolidines was accomplished. It was discovered that by using allylic amines and glyoxals at room temperature a cycloadduct was isolated bearing a 5-vinyl moiety. The results were promising and the first part of the project was to optimize the reaction followed by substrate scope expansion to build a library of compounds. The new cycloadducts could not have been synthesized under traditional methods due to side reactivity difficulties and therefore this work circumvents the problems associated with the classical routes. This is the first report of azomethine ylides derived from allylic amines and glyoxals to date. Many cycloadducts were synthesized and they all contained the 5-alkenyl group with many of them closely matching pyrrolidine containing natural products. The natural product, spirotryprostatin B, is an ideal target for featuring the developed methodology in total synthesis. Spirotryprostatin B was found to inhibit the G2/M phase in the cell replication pathway, suggesting a possible anti-cancer treatment. Using allylamine, ethyl glyoxylate, and appropriate dipolarophile under the optimized reaction conditions would afford a highly substituted cycloadduct that could be transformed into the final target. The core of the structure was synthesized in just three steps with only two steps requiring purification. The regio- and stereochemistry of the cycloadducts were analyzed using NOE enhancement and DFT studies to conclude that the [3+2] dipolar cycloaddition proceeded through the exo transition state. The total synthesis of the anti-cancer compound peducularine was also studied. Many different dipolarophiles were tested, but the ideal dipolarophile was not identified. The results of these experiments were important in defining the scope of the methodology. Advisors/Committee Members: Stephen P. Waters.

Subjects/Keywords: Chemistry; Organic Chemistry

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APA (6^th Edition):

Machamer, N. K. (2015). I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis. (Doctoral Dissertation). University of Vermont. Retrieved from https://scholarworks.uvm.edu/graddis/407

Chicago Manual of Style (16^th Edition):

Machamer, Natalie Kay. “I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis.” 2015. Doctoral Dissertation, University of Vermont. Accessed September 19, 2019. https://scholarworks.uvm.edu/graddis/407.

MLA Handbook (7^th Edition):

Machamer, Natalie Kay. “I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis.” 2015. Web. 19 Sep 2019.

Vancouver:

Machamer NK. I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis. [Internet] [Doctoral dissertation]. University of Vermont; 2015. [cited 2019 Sep 19]. Available from: https://scholarworks.uvm.edu/graddis/407.

Council of Science Editors:

Machamer NK. I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis. [Doctoral Dissertation]. University of Vermont; 2015. Available from: https://scholarworks.uvm.edu/graddis/407

14. Borikar, Sanjay P. Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates.

Degree: 2011, University of Pune

URL: http://shodhganga.inflibnet.ac.in/handle/10603/2375

► “Novel Organic Transformations Using Ultrasound, Ionic Liquid and Their Application Towards the Synthesis of Biological Active Molecules/Intermediates” Thesis is divided into three chapters: CHAPTER-1: Synthesis… (more)

Subjects/Keywords: Chemistry; Organic Chemistry

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APA (6^th Edition):

Borikar, S. P. (2011). Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates. (Thesis). University of Pune. Retrieved from http://shodhganga.inflibnet.ac.in/handle/10603/2375

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Borikar, Sanjay P. “Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates.” 2011. Thesis, University of Pune. Accessed September 19, 2019. http://shodhganga.inflibnet.ac.in/handle/10603/2375.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Borikar, Sanjay P. “Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates.” 2011. Web. 19 Sep 2019.

Vancouver:

Borikar SP. Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates. [Internet] [Thesis]. University of Pune; 2011. [cited 2019 Sep 19]. Available from: http://shodhganga.inflibnet.ac.in/handle/10603/2375.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Borikar SP. Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates. [Thesis]. University of Pune; 2011. Available from: http://shodhganga.inflibnet.ac.in/handle/10603/2375

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

15. Ayala, Malerie. Synthesis of a second generation naphthopyran metal-binding photoswitch.

Degree: 2015, California State University, Los Angeles

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=1597156

► The aim of this project was to increase the calcium binding affinity of our previously developed photochromic 3H-naphtho[2,1-b]pyran <b>1,</b> a light-controlled reversible binding switch… (more)

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

Ayala, M. (2015). Synthesis of a second generation naphthopyran metal-binding photoswitch. (Thesis). California State University, Los Angeles. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=1597156

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Ayala, Malerie. “Synthesis of a second generation naphthopyran metal-binding photoswitch.” 2015. Thesis, California State University, Los Angeles. Accessed September 19, 2019. http://pqdtopen.proquest.com/#viewpdf?dispub=1597156.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Ayala, Malerie. “Synthesis of a second generation naphthopyran metal-binding photoswitch.” 2015. Web. 19 Sep 2019.

Vancouver:

Ayala M. Synthesis of a second generation naphthopyran metal-binding photoswitch. [Internet] [Thesis]. California State University, Los Angeles; 2015. [cited 2019 Sep 19]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=1597156.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Ayala M. Synthesis of a second generation naphthopyran metal-binding photoswitch. [Thesis]. California State University, Los Angeles; 2015. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=1597156

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Purdue University

16. Kuriakose, Jerrin. Development of novel strategies to combat multidrug resistance mediated by efflux transporters and intracellular bacteria.

Degree: PhD, Chemistry, 2014, Purdue University

URL: http://docs.lib.purdue.edu/open_access_dissertations/312

► Multidrug resistance (MDR) is the condition where cancer cells or microorganisms cease to respond to multiple drugs. MDR conferred by efflux transporters, that deprive… (more)

Subjects/Keywords: Chemistry; Organic Chemistry

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APA (6^th Edition):

Kuriakose, J. (2014). Development of novel strategies to combat multidrug resistance mediated by efflux transporters and intracellular bacteria. (Doctoral Dissertation). Purdue University. Retrieved from http://docs.lib.purdue.edu/open_access_dissertations/312

Chicago Manual of Style (16^th Edition):

Kuriakose, Jerrin. “Development of novel strategies to combat multidrug resistance mediated by efflux transporters and intracellular bacteria.” 2014. Doctoral Dissertation, Purdue University. Accessed September 19, 2019. http://docs.lib.purdue.edu/open_access_dissertations/312.

MLA Handbook (7^th Edition):

Kuriakose, Jerrin. “Development of novel strategies to combat multidrug resistance mediated by efflux transporters and intracellular bacteria.” 2014. Web. 19 Sep 2019.

Vancouver:

Kuriakose J. Development of novel strategies to combat multidrug resistance mediated by efflux transporters and intracellular bacteria. [Internet] [Doctoral dissertation]. Purdue University; 2014. [cited 2019 Sep 19]. Available from: http://docs.lib.purdue.edu/open_access_dissertations/312.

Council of Science Editors:

Kuriakose J. Development of novel strategies to combat multidrug resistance mediated by efflux transporters and intracellular bacteria. [Doctoral Dissertation]. Purdue University; 2014. Available from: http://docs.lib.purdue.edu/open_access_dissertations/312

Wayne State University

17. Mandhapati, Appi Reddy. Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors.

Degree: 2016, Wayne State University

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=10153408

► AGAs are clinically important antibacterials for human therapy and have long been used as highly potent antibiotics for treating several bacterial infections. The fidelity… (more)

▼ AGAs are clinically important antibacterials for human therapy and have long been used as highly potent antibiotics for treating several bacterial infections. The fidelity of protein synthesis is affected by AGAs in the course of binding to specific sites of the bacterial rRNA. The clinical use of AGAs and their applications as therapeutics is restricted by toxicity (irreversible ototoxicity and reversible nephrotoxicity) and by the resistance of pathogens. The objective of this research was the development of proficient AGAs that are less toxic (i.e., more selective) and that evade resistance. The first three chapters of this thesis are aimed towards developing new aminoglycoside antibiotics with the emphasis on their chemical synthesis, and the biological evaluation of newly synthesized analogues, as well as the exploration of structure-activity relationships to understand the mechanism of their antimicrobial activity. In particular, studies have focused on the modification of the aminoglycosides apramycin and paromomycin so as to develop the next generation of potent AGAs. Chapter two reveals the importance of the 6' and <i>N</i>7' positions of the apramycin by investigation of the antibacterial activity and antiribosomal activity of the ten apramycin derivatives which were synthesized by modifying these locations. The effect of such modifications on antiribosomal activity is discussed in terms of their influence on drug binding to specific residues in the decoding A site. This information is useful in the development of a structure activity relationship for the antibacterial activity of the apramycin class of aminoglycosides and will also assist in the future design and development of more active and less toxic aminoglycoside antibiotics. Chapter three describes the structure-based design of an improved paromomycin derivative which carries an apramycin-like bicyclic ring I and a conformationally restricted hydroxyl or amine functionality. The influence of the bicyclic paromomycin 6'-hydroxy or amine groups on the binding pattern between AGA and bacterial RNA was investigated by using cell free translational assays. It was found that the bicyclic paromomycin derivative 155 with the equatorial 6’-hydroxy group has a better activity profile than parent paromomycin. In chapter four, an efficient sialyl donor was developed for the challenging α-sialylation by means of a highly electron withdrawing isothiocyanato group incorporated at C-5 position sialic acid. The isothiocyanato sialyl donor 218 proved to be an excellent α-directing group in sialylation for a wide range of acceptors, and provided high yields. Further, the sialylation of corresponding sialyl phosphate donor 231 was also demonstrated to give excellent selectivity, but yields are lower due to competing elimination. In addition, the rich chemistry of isothiocyanate functionality is explored to introduce a variety of novel functionalities at the 5-position of the sialosides including deamination, an alkyl…

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

Mandhapati, A. R. (2016). Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors. (Thesis). Wayne State University. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=10153408

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Mandhapati, Appi Reddy. “Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors.” 2016. Thesis, Wayne State University. Accessed September 19, 2019. http://pqdtopen.proquest.com/#viewpdf?dispub=10153408.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Mandhapati, Appi Reddy. “Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors.” 2016. Web. 19 Sep 2019.

Vancouver:

Mandhapati AR. Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors. [Internet] [Thesis]. Wayne State University; 2016. [cited 2019 Sep 19]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10153408.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Mandhapati AR. Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors. [Thesis]. Wayne State University; 2016. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10153408

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Toledo

18. Khatri, Hem Raj. Synthesis of Complex ortho-Allyliodoarenes via Reductive Iodonio-Claisen Rearrangement and Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A.

Degree: PhD, Chemistry, 2015, University of Toledo

URL: http://rave.ohiolink.edu/etdc/view?acc_num=toledo1431342601

► The chemistry related to hypervalent iodine compounds has been extensively studied in the past few decades due to the environmentally benign character of hypervalent iodine… (more)

▼ The chemistry related to hypervalent iodine compounds has been extensively studied in the past few decades due to the environmentally benign character of hypervalent iodine compounds. Most of those hypervalent iodanes-mediated chemical reactions involve the use of stoichiometric reagent and generate aryl iodide as a chemical waste, which makes the transformation a less atom economic processes. In the quest for more atom economic hypervalent iodine chemistry, we developed a reductive iodonio-Claisen rearrangement (RICR) involving ¿3-iodanes and allylsilanes in presence of Lewis acid to afford ortho-allyliodoarenes. It was found that an electron-donating group at the meta-position is required in order to favor the [3,3] sigmatropic rearrangement over reductive elimination. Moreover, the experimental results involving deuterated allylsilane support the reaction mechanism involving [3,3] sigmatropic rearrangement. The application of this method in organic synthesis has been demonstrated by converting ortho-allyliodoarenes into various building blocks such as benzofuran, dihydrobenzofuran, dihydrobenzopyran and indolines as well as by the concise synthesis of an antifungal natural product, broussin. We also developed Lewis acid-free RICR in which fluoroalcohols were used as the solvent and promoter.Angucycline antibiotics, the type of natural products bearing angularly assembled tetracyclic ring frame, have become a rapidly growing field of bioactive natural products in past few decades. Besides their interesting structural features, they possess widespread biological activities including antimicrobial, antiviral, and anticancer properties. The urdamycins are the class of angucyclines produced by Streptomyces fradiae and were first detected in chemical screening by Drautz and co-workers in 1986. Derhodinosylurdamycin A, obtained by methanolysis of urdamycin A, was first reported as a bioactive natural product derivative by Henkel and co-workers in 1986. It consists of an angucycline core with three 2,6-dideoxyhexoses comprising two D-olivose and one L-rhodinose, two with O-glycosidic linkage and one with C-glycosidic linkage to the aromatic core. Derhodinosylurdamycin A shows significant in-vitro activity against L1210 leukemia cell lines with IC50 value of 0.75µg/mL. Despite the interesting activities as well as structural intrigues, no total synthesis of derhodinosylurdamycin A has been accomplished thus far. Starting from commercially available starting materials, we have successfully completed the first enantioselective total synthesis of derhodinosylurdamycin A. Key steps in the synthesis include 1) a Hauser annulation between cyanophthalide and complex cyclohexenone to construct the tricyclic aryl iodide; 2) a palladium-catalyzed coupling between functionalized tetracyclic aryl iodide and D-rhamnal derived glycal stannane followed by reduction to form the ß-C-arylglycoside and 3) a late stage glycosylation between a disaccharide-derived glycosyl acetate donor and the ß-C-arylglycoside acceptor to afford the… Advisors/Committee Members: Zhu, Jianglong (Advisor).

Subjects/Keywords: Organic Chemistry; Chemistry

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APA (6^th Edition):

Khatri, H. R. (2015). Synthesis of Complex ortho-Allyliodoarenes via Reductive Iodonio-Claisen Rearrangement and Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A. (Doctoral Dissertation). University of Toledo. Retrieved from http://rave.ohiolink.edu/etdc/view?acc_num=toledo1431342601

Chicago Manual of Style (16^th Edition):

Khatri, Hem Raj. “Synthesis of Complex ortho-Allyliodoarenes via Reductive Iodonio-Claisen Rearrangement and Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A.” 2015. Doctoral Dissertation, University of Toledo. Accessed September 19, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1431342601.

MLA Handbook (7^th Edition):

Khatri, Hem Raj. “Synthesis of Complex ortho-Allyliodoarenes via Reductive Iodonio-Claisen Rearrangement and Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A.” 2015. Web. 19 Sep 2019.

Vancouver:

Khatri HR. Synthesis of Complex ortho-Allyliodoarenes via Reductive Iodonio-Claisen Rearrangement and Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A. [Internet] [Doctoral dissertation]. University of Toledo; 2015. [cited 2019 Sep 19]. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=toledo1431342601.

Council of Science Editors:

Khatri HR. Synthesis of Complex ortho-Allyliodoarenes via Reductive Iodonio-Claisen Rearrangement and Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A. [Doctoral Dissertation]. University of Toledo; 2015. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=toledo1431342601

University of Toledo

19. Starr, Matthew J. Synthesis of a C5'-Pseudouridinyl Radical Precursor.

Degree: MS, Medicinal Chemistry, 2015, University of Toledo

URL: http://rave.ohiolink.edu/etdc/view?acc_num=toledo1449675404

► Reactive oxygen species can cause damage to proteins, lipids, and nucleic acids through the generation of free radicals. Oxidative damage in DNA has been studied… (more)

Subjects/Keywords: Chemistry; Organic Chemistry

…precursors are made using synthetic organic chemistry to install special photolabile groups, such… …combined organic layers were dried using magnesium sulfate, and concentrated under reduced… …EtOAc (30 ml x 3), and the combined organic layers dried over magnesium sulfate. The crude was…

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APA (6^th Edition):

Starr, M. J. (2015). Synthesis of a C5'-Pseudouridinyl Radical Precursor. (Masters Thesis). University of Toledo. Retrieved from http://rave.ohiolink.edu/etdc/view?acc_num=toledo1449675404

Chicago Manual of Style (16^th Edition):

Starr, Matthew J. “Synthesis of a C5'-Pseudouridinyl Radical Precursor.” 2015. Masters Thesis, University of Toledo. Accessed September 19, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1449675404.

MLA Handbook (7^th Edition):

Starr, Matthew J. “Synthesis of a C5'-Pseudouridinyl Radical Precursor.” 2015. Web. 19 Sep 2019.

Vancouver:

Starr MJ. Synthesis of a C5'-Pseudouridinyl Radical Precursor. [Internet] [Masters thesis]. University of Toledo; 2015. [cited 2019 Sep 19]. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=toledo1449675404.

Council of Science Editors:

Starr MJ. Synthesis of a C5'-Pseudouridinyl Radical Precursor. [Masters Thesis]. University of Toledo; 2015. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=toledo1449675404

University of Toledo

20. Baryal, Kedar N. Stereoselective Synthesis of Digitoxin and S-Linked Glycosides.

Degree: PhD, Chemistry, 2016, University of Toledo

URL: http://rave.ohiolink.edu/etdc/view?acc_num=toledo1438174529

► Deoxy-sugars are an important class of carbohydrates in which one or more hydroxyl group/s are replaced by hydrogen atom/s. 2-Deoxy sugars exist in a wide… (more)

▼ Deoxy-sugars are an important class of carbohydrates in which one or more hydroxyl group/s are replaced by hydrogen atom/s. 2-Deoxy sugars exist in a wide range of bioactive natural products and clinical agents including antimicrobial and antitumor antibiotics. These sugars play critical roles in biological activity by serving as additional binding sites or changing the pharmacokinetics of molecules. Digitoxin is a cardiac glycoside isolated from Digitalis purpurea and has been in use for the treatment of congestive heart failure and cardiac arrhythmia for a long period of time. However, the clinical use of digitoxin is limited due to the narrow therapeutic window. Over the years, antiproliferative activity against cancer cells has been known and recently, more attention has focused on the direction of this research. Structurally, digitoxin contains two subunits: ß-linked digitoxose trisaccharide and aglycon (digitoxigenin). In this study, we described a rhenium(V)-catalyzed stereoselective synthesis of ß-D-digitoxosides from 6-deoxy-D-allal. The ß-selectivity may be due to the disfavored formation of a-D-digitoxosides by 1,3-diaxial interactions. In addition, Re(V)-catalysis had been applied to the synthesis of the digitoxin trisaccharide glycal for the direct synthesis of digitoxin and C1'-epi-digitoxin.Moreover, the O-glycosidic linkage of 2-deoxy glycosides is known to be susceptible to acid hydrolysis and enzymatic cleavage, which results in the increased toxicity and reduced activity of the parent molecules. Thioglycosides (S-linked glycosides), in which the glycosidic oxygen is replaced by a sulfur atom, are carbohydrate mimics resistant towards chemical and enzymatic cleavage. In addition, thioglycosides maintain the biological activity of their parent O-glycosides. Therefore, it is appealing to synthesize S-linked 2-deoxy sugars and comparatively study their chemical and biological properties with their O-linked counterparts. Due to the absence of a directing group at C-2, stereoselective synthesis of S-linked 2-deoxy sugars is challenging. To overcome this problem, we devised the sulfenylation of stereochemically defined glycosyl lithium with sugar-derived asymmetric disulfides to furnish S-linked 2-deoxy a- and ß-glycosides in excellent yield and stereoselectivity. The stereochemically defined 2-deoxy glycosyl lithiums can be readily formed by reductive lithiation of glycosylphenylsulfide at low temperature by lithium di-4,4’-tert-butylbiphenylide (LiDBB) and subsequent temperature-controlled anomerization. A complex S-linked trisaccharide, and a hexasaccharide analog of landomycin A have been successfully synthesized by employing this newly developed method. Advisors/Committee Members: Zhu, Jianglong (Committee Chair).

Subjects/Keywords: Chemistry; Organic Chemistry

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APA (6^th Edition):

Baryal, K. N. (2016). Stereoselective Synthesis of Digitoxin and S-Linked Glycosides. (Doctoral Dissertation). University of Toledo. Retrieved from http://rave.ohiolink.edu/etdc/view?acc_num=toledo1438174529

Chicago Manual of Style (16^th Edition):

Baryal, Kedar N. “Stereoselective Synthesis of Digitoxin and S-Linked Glycosides.” 2016. Doctoral Dissertation, University of Toledo. Accessed September 19, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1438174529.

MLA Handbook (7^th Edition):

Baryal, Kedar N. “Stereoselective Synthesis of Digitoxin and S-Linked Glycosides.” 2016. Web. 19 Sep 2019.

Vancouver:

Baryal KN. Stereoselective Synthesis of Digitoxin and S-Linked Glycosides. [Internet] [Doctoral dissertation]. University of Toledo; 2016. [cited 2019 Sep 19]. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=toledo1438174529.

Council of Science Editors:

Baryal KN. Stereoselective Synthesis of Digitoxin and S-Linked Glycosides. [Doctoral Dissertation]. University of Toledo; 2016. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=toledo1438174529

University of California – Irvine

21. Daub, Mary Elisabeth. A Unified Synthetic Approach Toward the Kalihinanes.

Degree: Chemistry, 2016, University of California – Irvine

URL: http://www.escholarship.org/uc/item/5133j2rr

► This dissertation describes our efforts toward developing a unified synthesis of the kalininane family of antimalarial marine isocyanoterpenes. Chapter 1 focuses on the isolation, structure… (more)

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

Daub, M. E. (2016). A Unified Synthetic Approach Toward the Kalihinanes. (Thesis). University of California – Irvine. Retrieved from http://www.escholarship.org/uc/item/5133j2rr

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Daub, Mary Elisabeth. “A Unified Synthetic Approach Toward the Kalihinanes.” 2016. Thesis, University of California – Irvine. Accessed September 19, 2019. http://www.escholarship.org/uc/item/5133j2rr.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Daub, Mary Elisabeth. “A Unified Synthetic Approach Toward the Kalihinanes.” 2016. Web. 19 Sep 2019.

Vancouver:

Daub ME. A Unified Synthetic Approach Toward the Kalihinanes. [Internet] [Thesis]. University of California – Irvine; 2016. [cited 2019 Sep 19]. Available from: http://www.escholarship.org/uc/item/5133j2rr.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Daub ME. A Unified Synthetic Approach Toward the Kalihinanes. [Thesis]. University of California – Irvine; 2016. Available from: http://www.escholarship.org/uc/item/5133j2rr

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of California – San Diego

22. Hamill, Kristina. Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters.

Degree: Chemistry, 2016, University of California – San Diego

URL: http://www.escholarship.org/uc/item/9p90k8s4

► High molecular weight and highly-charged biomolecules are emerging as drugs with high selectivity and efficacy; however, new strategies are needed to improve their efficiency and… (more)

▼ High molecular weight and highly-charged biomolecules are emerging as drugs with high selectivity and efficacy; however, new strategies are needed to improve their efficiency and targeted delivery in biological systems. One potential solution is the conjugation or association of the biologic with a molecular transporter. Inspired by proteins, such as HIV-Tat, with cellular translocation abilities, numerous guanidinium-rich molecular transporters have been synthesized from a diverse range of nonpeptidic scaffolds. While their repertoire has expanded tremendously in the past two decades, new transporters can provide unique intracellular distributions, targeting effects, or pharmacological properties. Polymyxin B is a cyclic polypeptide antibiotic containing five primary amines and a hydrophobic tail that has not been exploited as a delivery module. Here, we synthesized functionalized derivatives of polymyxin and its per-guanidinylated derivative and evaluated their cellular uptake in mammalian cells. Both polymyxin and its guanidinylated form effectively enter mammalian cells at nanomolar concentrations and can facilitate the cellular delivery of large biomolecules and liposomal assemblies. Guanidinoglycosides are a non-oligomeric class of molecular transporters developed in our lab that permeate the cell membrane through heparan sulfate-dependent pathways at low nanomolar concentrations. To further advance guanidinoglycosides as transporters, guanidinylated neomycin (GNeo) derivatives containing different fatty acids were synthesized and incorporated into liposomes. A small molecule dye or a lysosomal enzyme were encapsulated in the liposomes and delivered to Chinese hamster ovary cells or human fibroblasts, respectively. Incorporation of stearyl- or di-oleyl-GNeo lipids into liposomes resulted in the greatest enhancement of uptake. The delivery of α-L-iduronidase, a lysosomal enzyme, was able to restore enzyme function in fibroblasts lacking endogenous enzyme. As an alternative approach to enhance GNeo as a molecular transporter, oligomers of GNeo were synthesized using ring-opening metathesis polymerization. The synthesis of the reactive monomer, formation of GNeo oligomers, and preliminary cellular uptake studies are presented. In addition to using GNeo for new delivery systems, we also sought to explore the effect the linker connecting the cargo to the carrier has on conjugation and uptake. Varying the length and hydrophobic properties of the linker joining GNeo to biotin resulted in diverse conjugation efficiencies to streptavidin and differences in cellular uptake, highlighting the importance of the linker when designing and studying new molecular transporters.

Subjects/Keywords: Organic chemistry; Chemistry

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APA (6^th Edition):

Hamill, K. (2016). Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters. (Thesis). University of California – San Diego. Retrieved from http://www.escholarship.org/uc/item/9p90k8s4

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Hamill, Kristina. “Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters.” 2016. Thesis, University of California – San Diego. Accessed September 19, 2019. http://www.escholarship.org/uc/item/9p90k8s4.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Hamill, Kristina. “Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters.” 2016. Web. 19 Sep 2019.

Vancouver:

Hamill K. Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters. [Internet] [Thesis]. University of California – San Diego; 2016. [cited 2019 Sep 19]. Available from: http://www.escholarship.org/uc/item/9p90k8s4.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Hamill K. Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters. [Thesis]. University of California – San Diego; 2016. Available from: http://www.escholarship.org/uc/item/9p90k8s4

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of California – Riverside

23. Bastin, Baback. Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs.

Degree: Chemistry, 2015, University of California – Riverside

URL: http://www.escholarship.org/uc/item/68x2v2nr

► Identifying enzyme mechanisms at proton level resolution is the ultimate goal of enzymology. Traditional enzyme mechanistic studies infer protonation states from x-ray crystal structure and… (more)

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

Bastin, B. (2015). Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs. (Thesis). University of California – Riverside. Retrieved from http://www.escholarship.org/uc/item/68x2v2nr

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Bastin, Baback. “Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs.” 2015. Thesis, University of California – Riverside. Accessed September 19, 2019. http://www.escholarship.org/uc/item/68x2v2nr.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Bastin, Baback. “Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs.” 2015. Web. 19 Sep 2019.

Vancouver:

Bastin B. Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs. [Internet] [Thesis]. University of California – Riverside; 2015. [cited 2019 Sep 19]. Available from: http://www.escholarship.org/uc/item/68x2v2nr.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Bastin B. Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs. [Thesis]. University of California – Riverside; 2015. Available from: http://www.escholarship.org/uc/item/68x2v2nr

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

UCLA

24. He, Cyndi Qixin. Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions.

Degree: Chemistry, 2013, UCLA

URL: http://www.escholarship.org/uc/item/4g93x5sn

► Transannular Diels-Alder (TADA) reactions are a powerful tool for the construction of polycyclic structures with four stereogenic centers. A series of remarkably facile and stereoselective… (more)

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

He, C. Q. (2013). Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions. (Thesis). UCLA. Retrieved from http://www.escholarship.org/uc/item/4g93x5sn

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

He, Cyndi Qixin. “Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions.” 2013. Thesis, UCLA. Accessed September 19, 2019. http://www.escholarship.org/uc/item/4g93x5sn.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

He, Cyndi Qixin. “Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions.” 2013. Web. 19 Sep 2019.

Vancouver:

He CQ. Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions. [Internet] [Thesis]. UCLA; 2013. [cited 2019 Sep 19]. Available from: http://www.escholarship.org/uc/item/4g93x5sn.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

He CQ. Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions. [Thesis]. UCLA; 2013. Available from: http://www.escholarship.org/uc/item/4g93x5sn

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Washington University in St. Louis

25. Lu, Guojian. Part I Development of Nucleophilic Acylation Catalysts Part II Chiral Brønsted Acid Catalyzed Enantioselective Alcoholysis.

Degree: PhD, Chemistry, 2011, Washington University in St. Louis

URL: https://openscholarship.wustl.edu/etd/612

► Chiral bicyclic amidines and isothioureas developed in our group have been showed as a new type of nucleophilic acyl transfer catalysts. Based on the… (more)

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

Lu, G. (2011). Part I Development of Nucleophilic Acylation Catalysts Part II Chiral Brønsted Acid Catalyzed Enantioselective Alcoholysis. (Doctoral Dissertation). Washington University in St. Louis. Retrieved from https://openscholarship.wustl.edu/etd/612

Chicago Manual of Style (16^th Edition):

Lu, Guojian. “Part I Development of Nucleophilic Acylation Catalysts Part II Chiral Brønsted Acid Catalyzed Enantioselective Alcoholysis.” 2011. Doctoral Dissertation, Washington University in St. Louis. Accessed September 19, 2019. https://openscholarship.wustl.edu/etd/612.

MLA Handbook (7^th Edition):

Lu, Guojian. “Part I Development of Nucleophilic Acylation Catalysts Part II Chiral Brønsted Acid Catalyzed Enantioselective Alcoholysis.” 2011. Web. 19 Sep 2019.

Vancouver:

Lu G. Part I Development of Nucleophilic Acylation Catalysts Part II Chiral Brønsted Acid Catalyzed Enantioselective Alcoholysis. [Internet] [Doctoral dissertation]. Washington University in St. Louis; 2011. [cited 2019 Sep 19]. Available from: https://openscholarship.wustl.edu/etd/612.

Council of Science Editors:

Lu G. Part I Development of Nucleophilic Acylation Catalysts Part II Chiral Brønsted Acid Catalyzed Enantioselective Alcoholysis. [Doctoral Dissertation]. Washington University in St. Louis; 2011. Available from: https://openscholarship.wustl.edu/etd/612

Duke University

26. Brooner, Rachel. Mechanistic Studies of pi-Activation Catalysis by Cationic Gold(I) and Brønsted-acid .

Degree: 2013, Duke University

URL: http://hdl.handle.net/10161/8070

► Soluble gold(I) complexes are highly efficient catalysts for the functionalization of C-C multiple bonds through the addition of carbon- or heteroatom-nucleophiles across π-bonds or… (more)

▼ Soluble gold(I) complexes are highly efficient catalysts for the functionalization of C-C multiple bonds through the addition of carbon- or heteroatom-nucleophiles across π-bonds or cycloisomerizations of enynes and related π-systems. Mechanisms involving outer-sphere attack of a nucleophile on the electrophilic π-ligand of a cationic gold π-complex are typically invoked for gold(I)-catalyzed hydrofunctionalization and cycloisomerization processes, but direct experimental evidence for this mechanism is limited. As an extension of the pioneering research in the Widenhoefer lab on the synthesis and characterization of gold(I) π-complexes, a diverse family of 15 gold(I) π-complexes in three distinct series are reported herein. First, the synthesis, characterization, and solution behavior of a series of seven gold(I) π-diene complexes is reported. In each case, gold binds preferentially to the less substituted C═C bond of the diene, but intermolecular exchange of the complexed and uncomplexed C═C is facile. The gold-alkene interaction is stabilized via substitution-dependant donation of electron density from the uncomplexed C═C bond to the complexed C═C bond of the diene. In addition, a pair of axially chiral dicationic, bis(gold) π-alkene complexes that contain a 2,2′-bis(phosphino)biphenyl ligand are reported. The complexes show no intramolecular Au-Au interactions or facial selectivity for complexation, but solution analyses suggest that the environment about one gold center affects the behavior of the proximal gold center through a yet unknown mechanism. Gold(I) π-alkene, alkyne, diene, and allene complexes that bear a triphenylphosphine supporting ligand have also been synthesized and characterized in situ. The π-ligands in the triphenylphosphine gold complexes were considerably more labile than those bearing bulky, electron rich phosphine or N-heterocyclic carbene ligands, and the complexes decomposed in solution above -20 °C. Mechanistic investigation of the gold-catalyzed cycloisomerization of a 7-aryl-1,6-enyne led to characterization of the first organometallic complex directly observed in the course of an enyne cycloisomerization. The complex is best described as a gold π-(bicyclo[3.2.0]heptane) complex with a domination metallacyclopropane binding interaction and undergoes an acid-catalyzed rearrangement to yield a stable bicyclo[3.2.0]heptane product which can further isomerize in the presence of Ag+. In a further effort to understand the reactive species in catalytic cycloisomerizations, the first example of a gold cyclopropyl carbene was synthesized and fully characterized. Finally, in an effort understand the mechanistic distinctions between electrophilic metal-catalyzed hydrofunctionalization and similar Brønsted acid-catalyzed additions, the kinetics and stereochemistry of intramolucar acid-catalyzed hydrofunctionalizion were studied. In all cases, the transformations were > 95 % selective for… Advisors/Committee Members: Widenhoefer, Ross A (advisor).

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

Brooner, R. (2013). Mechanistic Studies of pi-Activation Catalysis by Cationic Gold(I) and Brønsted-acid . (Thesis). Duke University. Retrieved from http://hdl.handle.net/10161/8070

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Brooner, Rachel. “Mechanistic Studies of pi-Activation Catalysis by Cationic Gold(I) and Brønsted-acid .” 2013. Thesis, Duke University. Accessed September 19, 2019. http://hdl.handle.net/10161/8070.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Brooner, Rachel. “Mechanistic Studies of pi-Activation Catalysis by Cationic Gold(I) and Brønsted-acid .” 2013. Web. 19 Sep 2019.

Vancouver:

Brooner R. Mechanistic Studies of pi-Activation Catalysis by Cationic Gold(I) and Brønsted-acid . [Internet] [Thesis]. Duke University; 2013. [cited 2019 Sep 19]. Available from: http://hdl.handle.net/10161/8070.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Brooner R. Mechanistic Studies of pi-Activation Catalysis by Cationic Gold(I) and Brønsted-acid . [Thesis]. Duke University; 2013. Available from: http://hdl.handle.net/10161/8070

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Duke University

27. Robertson, Bradley. I. The Asymmetric Total Synthesis of Apratoxin D II. Studies in the Gold(I)-Catalyzed Cycloisomerization of 7-Aryl-1,6-Enynes. III. Synthesis and Application of Multidentate Ligands Toward the Realization of Fluxional Mechanocatalysis .

Degree: 2015, Duke University

URL: http://hdl.handle.net/10161/11348

► Apratoxin D, recently isolated from two species of cyanobacteria, L. majuscula and L. sordida, exhibits highly potent in vitro cytotoxicity against H-‐‑460 human lung… (more)

▼ Apratoxin D, recently isolated from two species of cyanobacteria, L. majuscula and L. sordida, exhibits highly potent in vitro cytotoxicity against H-‐‑460 human lung cancer cells with an IC50 value of 2.6 nM. The potent biological activity exhibited by apratoxin D combined with its intriguing molecular architecture has led to the pursuit of its asymmetric total synthesis. Studies toward and completion of the first asymmetric total synthesis of apratoxin D are reported. Key transformations include a Kelly thiazoline formation, Paterson anti-‐‑aldol and an Evans syn-‐‑aldol. The synthesis was completed in 2.1% total yield over 31 steps from (R)-‐‑citronellic acid. Cationic gold (I) complexes are highly efficient catalysts for the cycloisomerization of 1,6-‐‑enynes, a transformation capable of providing a great amount of structural complexity from simple starting materials. The in situ spectroscopic analysis of the catalytic cycloisomerization of a 7-‐‑phenyl-‐‑1,6-‐‑enyne, as well as the tandem gold/silver-‐‑catalyzed cycloaddition/hydroarylation of 7-‐‑aryl-‐‑1,6-‐‑enynes is described. The cycloaddition/hydroarylation reaction provides 6,6-‐‑ diarylbicyclo[3.2.0]heptanes in good yield under mild conditions. Experimental observations point to a mechanism involving gold-‐‑catalyzed cycloaddition followed by silver-‐‑catalyzed hydroarylation of a bicyclo[3.2.0]hept-‐‑1(7)-‐‑ene intermediate. The control of bond scission and formation by mechanocatalysis has potential in a variety of applications, including biomedical devices, mechanical sensors and self-‐‑ 6 healing materials. The synthesis and study of C2-‐‑symmetric bis(phosphine) ligands with applications toward mechanocatalysis is described. Additionally, the synthesis and study of a tetradentate ligand designed toward mechanochemical activation of a latent catalytic complex is reported. These studies have allowed further development in the design of transition metal complexes capable of activation by mechanical force. Advisors/Committee Members: Widenhoefer, Ross A (advisor).

Subjects/Keywords: Chemistry; Organic chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Robertson, B. (2015). I. The Asymmetric Total Synthesis of Apratoxin D II. Studies in the Gold(I)-Catalyzed Cycloisomerization of 7-Aryl-1,6-Enynes. III. Synthesis and Application of Multidentate Ligands Toward the Realization of Fluxional Mechanocatalysis . (Thesis). Duke University. Retrieved from http://hdl.handle.net/10161/11348

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Robertson, Bradley. “I. The Asymmetric Total Synthesis of Apratoxin D II. Studies in the Gold(I)-Catalyzed Cycloisomerization of 7-Aryl-1,6-Enynes. III. Synthesis and Application of Multidentate Ligands Toward the Realization of Fluxional Mechanocatalysis .” 2015. Thesis, Duke University. Accessed September 19, 2019. http://hdl.handle.net/10161/11348.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Robertson, Bradley. “I. The Asymmetric Total Synthesis of Apratoxin D II. Studies in the Gold(I)-Catalyzed Cycloisomerization of 7-Aryl-1,6-Enynes. III. Synthesis and Application of Multidentate Ligands Toward the Realization of Fluxional Mechanocatalysis .” 2015. Web. 19 Sep 2019.

Vancouver:

Robertson B. I. The Asymmetric Total Synthesis of Apratoxin D II. Studies in the Gold(I)-Catalyzed Cycloisomerization of 7-Aryl-1,6-Enynes. III. Synthesis and Application of Multidentate Ligands Toward the Realization of Fluxional Mechanocatalysis . [Internet] [Thesis]. Duke University; 2015. [cited 2019 Sep 19]. Available from: http://hdl.handle.net/10161/11348.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Robertson B. I. The Asymmetric Total Synthesis of Apratoxin D II. Studies in the Gold(I)-Catalyzed Cycloisomerization of 7-Aryl-1,6-Enynes. III. Synthesis and Application of Multidentate Ligands Toward the Realization of Fluxional Mechanocatalysis . [Thesis]. Duke University; 2015. Available from: http://hdl.handle.net/10161/11348

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

28. Shadrick, Melanie. Effect of C-7,8 di-Picoloyl in Sialylation Reactions.

Degree: 2018, Southern Illinois University at Edwardsville

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=10808011

► N-acetyl neuraminic acid is most common member of the sialic acid family. This unique monosaccharide is displayed at the terminal position of oligosaccharides in… (more)

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

Shadrick, M. (2018). Effect of C-7,8 di-Picoloyl in Sialylation Reactions. (Thesis). Southern Illinois University at Edwardsville. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=10808011

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Shadrick, Melanie. “Effect of C-7,8 di-Picoloyl in Sialylation Reactions.” 2018. Thesis, Southern Illinois University at Edwardsville. Accessed September 19, 2019. http://pqdtopen.proquest.com/#viewpdf?dispub=10808011.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Shadrick, Melanie. “Effect of C-7,8 di-Picoloyl in Sialylation Reactions.” 2018. Web. 19 Sep 2019.

Vancouver:

Shadrick M. Effect of C-7,8 di-Picoloyl in Sialylation Reactions. [Internet] [Thesis]. Southern Illinois University at Edwardsville; 2018. [cited 2019 Sep 19]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10808011.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Shadrick M. Effect of C-7,8 di-Picoloyl in Sialylation Reactions. [Thesis]. Southern Illinois University at Edwardsville; 2018. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10808011

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

29. Lippincott, Daniel John. Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature...

Degree: 2019, University of California, Santa Barbara

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=10982306

► I. An environmentally responsible, mild method for the synthesis of functionalized 1,3-butadienes is presented. It utilizes allenic esters of varying substitution patterns, as well… (more)

Subjects/Keywords: Chemistry; Organic chemistry

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APA (6^th Edition):

Lippincott, D. J. (2019). Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature... (Thesis). University of California, Santa Barbara. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=10982306

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Lippincott, Daniel John. “Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature...” 2019. Thesis, University of California, Santa Barbara. Accessed September 19, 2019. http://pqdtopen.proquest.com/#viewpdf?dispub=10982306.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Lippincott, Daniel John. “Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature...” 2019. Web. 19 Sep 2019.

Vancouver:

Lippincott DJ. Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature... [Internet] [Thesis]. University of California, Santa Barbara; 2019. [cited 2019 Sep 19]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10982306.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Lippincott DJ. Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature... [Thesis]. University of California, Santa Barbara; 2019. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10982306

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Kansas

30. Yang, Ming-Hsiu. Synthetic Strategies to Access Biologically Important Fluorinated Motifs: Fluoroalkenes and Difluoroketones.

Degree: PhD, Medicinal Chemistry, 2017, University of Kansas

URL: http://hdl.handle.net/1808/26158

► Fluorine plays an important role in drug design, because of some unique features imparted by fluorine. The incorporation of fluorine into small molecules can modulate… (more)

▼ Fluorine plays an important role in drug design, because of some unique features imparted by fluorine. The incorporation of fluorine into small molecules can modulate molecular physicochemical properties, metabolic stability, lipophilicity, and binding affinity to the target proteins. However, few fluorinated molecules are biosynthesized by enzymes. This means incorporating fluorine into the molecules relies on synthetic methods. Thus, efficient synthetic strategies to access the molecules bearing a variety of privileged fluorinated moieties are important for drug discovery. Fluoroalkenes are an isopolar and isosteric mimic of an amide bond with distinct biophysical properties, including decreased H-bond donating and accepting abilities, increased lipophilicity, and metabolic stability. Moreover, fluoroalkenes can also serve as probes for conducting conformational analyses of amides. These potential applications require the development of efficient methods to access fluoroalkenes. In chapter 2, a Shapiro fluorination strategy to access peptidomimetic fluoroalkenes is demonstrated. The Shapiro fluorination reactions convert a ketone into a fluoroalkene in one or two steps. Moreover, this method uses inexpensive and readily available reagents, and no transition metals are involved in the reactions. Thus, it provides an operation-simple alternative to access fluoroalkenes in medicinal chemistry. a,a-difluoroketones represent a privileged substructure in medicinal chemistry, and serves as inhibitors to many hydrolytic enzymes, such as serine and aspartyl proteases. From chapters 3 to 5, palladium-catalyzed decarboxylative methods are developed for accessing a-alkyl- and a-aryl-a,a-difluoroketones. This decarboxylative strategy overcomes two major challenges associated with alkylation reactions of a,a-difluoroketone enolates. Chapter 3 demonstrates that decarboxylation regioselectively generates a,a-difluoroketone enolates, which are difficult to access by base deprotonation. Moreover, palladium catalysis enables the coupling of the a,a-difluoroketone enolate with benzylic electrophiles to form a key C(a)–C(sp3) bond. In chapter 4, an orthogonal catalytic system is developed for accessing linear and branched a-allyl-a,a-difluoroketones. Two distinct mechanisms are involved in the formation of the regioisomers. Chapter 5 describes a base-mediated selective para-C–H difluoroalkylation of arenes, which represents a different strategy for para-C–H functionalization of arenes compared to the known methods. These decarboxylative coupling reactions provide structurally diverse a,a-difluoroketone derivatives, and should be useful for accessing potential biological probes and therapeutics. Advisors/Committee Members: Altman, Ryan A (advisor), Clift, Michael D (cmtemember), Dutta, Apurba (cmtemember), Rafferty, Michael F (cmtemember), Tunge, Jon A (cmtemember).

Subjects/Keywords: Organic chemistry; Chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Yang, M. (2017). Synthetic Strategies to Access Biologically Important Fluorinated Motifs: Fluoroalkenes and Difluoroketones. (Doctoral Dissertation). University of Kansas. Retrieved from http://hdl.handle.net/1808/26158

Chicago Manual of Style (16^th Edition):

Yang, Ming-Hsiu. “Synthetic Strategies to Access Biologically Important Fluorinated Motifs: Fluoroalkenes and Difluoroketones.” 2017. Doctoral Dissertation, University of Kansas. Accessed September 19, 2019. http://hdl.handle.net/1808/26158.

MLA Handbook (7^th Edition):

Yang, Ming-Hsiu. “Synthetic Strategies to Access Biologically Important Fluorinated Motifs: Fluoroalkenes and Difluoroketones.” 2017. Web. 19 Sep 2019.

Vancouver:

Yang M. Synthetic Strategies to Access Biologically Important Fluorinated Motifs: Fluoroalkenes and Difluoroketones. [Internet] [Doctoral dissertation]. University of Kansas; 2017. [cited 2019 Sep 19]. Available from: http://hdl.handle.net/1808/26158.

Council of Science Editors:

Yang M. Synthetic Strategies to Access Biologically Important Fluorinated Motifs: Fluoroalkenes and Difluoroketones. [Doctoral Dissertation]. University of Kansas; 2017. Available from: http://hdl.handle.net/1808/26158

Open Access Theses and Dissertations