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You searched for subject:(indolidene). Showing records 1 – 2 of 2 total matches.

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Penn State University

1. Gonzalez, Inanllely Y. INTRAMOLECULAR [3 + 2] CYCLOCONDENSATIONS OF ALKENES WITH INDOLIDENE AND INDOLIDENIUM CATION INTERMEDIATES: APPLICATION TOWARDS THE SYNTHESIS OF LECANINDOLE D.

Degree: 2017, Penn State University

An allenyl azide cyclization reaction was developed to access the skeleton of the indolosesquiterpene family of natural products, while addressing the challenges of synthesizing indole-fused trans hydrindanes. This cyclization cascade is triggered by the irradiation of an allenyl azide functionality and is presumed to go through a highly reactive indolidene intermediate. This electrophilic indolidene intermediate is then trapped by a pendant alkene nucleophile to afford a tetracyclic adduct, containing an indole-fused trans hydrindane unit. In addition, a Lewis acid-mediated bicyclization also was explored involving the solvolysis of indole 2-(methyl alcohol) derivatives to deliver indolidenium cation intermediates, which also are trapped by alkene nucleophiles. Regiochemical and stereochemical questions for both cyclization strategies, as well as efforts to favor C–C bond forming products, have been explored. The application of the photochemical [3 + 2] cyclization reaction was demonstrated in the synthesis of the indolosesquiterpene core of lecanindole D, a potent and selective agonist for the human progesterone receptor. Efforts towards the total synthesis of lecanindole D also are discussed, including the installation of the challenging vicinal all carbon stereogenic centers. Advisors/Committee Members: Ken S. Feldman, Dissertation Advisor/Co-Advisor, Ken S. Feldman, Committee Chair/Co-Chair, Scott T. Phillips, Committee Member, Ray L. Funk, Committee Member, Michael Hickner, Outside Member.

Subjects/Keywords: cyclizations; indolidene; cyclocondensation

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

APA (6th Edition):

Gonzalez, I. Y. (2017). INTRAMOLECULAR [3 + 2] CYCLOCONDENSATIONS OF ALKENES WITH INDOLIDENE AND INDOLIDENIUM CATION INTERMEDIATES: APPLICATION TOWARDS THE SYNTHESIS OF LECANINDOLE D. (Thesis). Penn State University. Retrieved from https://submit-etda.libraries.psu.edu/catalog/13762izg105

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

Chicago Manual of Style (16th Edition):

Gonzalez, Inanllely Y. “INTRAMOLECULAR [3 + 2] CYCLOCONDENSATIONS OF ALKENES WITH INDOLIDENE AND INDOLIDENIUM CATION INTERMEDIATES: APPLICATION TOWARDS THE SYNTHESIS OF LECANINDOLE D.” 2017. Thesis, Penn State University. Accessed November 29, 2020. https://submit-etda.libraries.psu.edu/catalog/13762izg105.

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

MLA Handbook (7th Edition):

Gonzalez, Inanllely Y. “INTRAMOLECULAR [3 + 2] CYCLOCONDENSATIONS OF ALKENES WITH INDOLIDENE AND INDOLIDENIUM CATION INTERMEDIATES: APPLICATION TOWARDS THE SYNTHESIS OF LECANINDOLE D.” 2017. Web. 29 Nov 2020.

Vancouver:

Gonzalez IY. INTRAMOLECULAR [3 + 2] CYCLOCONDENSATIONS OF ALKENES WITH INDOLIDENE AND INDOLIDENIUM CATION INTERMEDIATES: APPLICATION TOWARDS THE SYNTHESIS OF LECANINDOLE D. [Internet] [Thesis]. Penn State University; 2017. [cited 2020 Nov 29]. Available from: https://submit-etda.libraries.psu.edu/catalog/13762izg105.

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

Council of Science Editors:

Gonzalez IY. INTRAMOLECULAR [3 + 2] CYCLOCONDENSATIONS OF ALKENES WITH INDOLIDENE AND INDOLIDENIUM CATION INTERMEDIATES: APPLICATION TOWARDS THE SYNTHESIS OF LECANINDOLE D. [Thesis]. Penn State University; 2017. Available from: https://submit-etda.libraries.psu.edu/catalog/13762izg105

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


Penn State University

2. Hester II, David Keith. PART I. EXTENDING ALLENYL AZIDE CYCLOADDITION CHEMISTRY: PHOTOCHEMISTRY AND CU(I) MEDIATION. PART II. EFFORTS TOWARD THE TOTAL SYNTHESIS OF (-)-KINAMYCIN F. PART III. EFFECT OF STRENGTH AND SYMMETRY OF HYDROGEN BONDS ON QUINONE REDUCTION POTENTIAL.

Degree: 2008, Penn State University

Photochemical irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess CuI furnished functionalized 2,3-cyclopentenylindoles in good yield with only trace amounts of C-N bonded regioisomers. These results represent a significant departure from the modest-to-nonexistent regioselectivity observed upon thermolysis of these same substrates. The scope and limitation of this methodology is discussed. Mechanistic insight was aided by a collaborative effort with DFT computational models. These studies suggest that the allenyl azide cyclization cascade proceeds through a highly reactive indolidene intermediate. A synthetic effort toward the synthesis of the fischerindole class of natural products utilizing this methodology is also discussed. A total synthesis effort toward the diazoparaquinone natural product (-)-kinamycin F is reported. A strategy utilizing a Hauser annulation to assemble the core tetracycle is employed. A series of 11 simple naphthoquinone derivatives featuring H-bond donor amides at one or both peri positions were prepared and some salient physical properties were measured. A correlation between both IR frequency and NMR peak position, as indicators of internal H-bond strength, and the quinone single electron reduction potential was observed. Advisors/Committee Members: Ken S Feldman, Committee Chair/Co-Chair, John H Golbeck, Committee Chair/Co-Chair, Steven M Weinreb, Committee Member, Ming Tien, Committee Member.

Subjects/Keywords: methodology; synthesis; photosystem I; internally hydrogen-bonded quinone; indolidene; kinamycin; fischerindole; Allenyl Azide; photochemistry

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

APA (6th Edition):

Hester II, D. K. (2008). PART I. EXTENDING ALLENYL AZIDE CYCLOADDITION CHEMISTRY: PHOTOCHEMISTRY AND CU(I) MEDIATION. PART II. EFFORTS TOWARD THE TOTAL SYNTHESIS OF (-)-KINAMYCIN F. PART III. EFFECT OF STRENGTH AND SYMMETRY OF HYDROGEN BONDS ON QUINONE REDUCTION POTENTIAL. (Thesis). Penn State University. Retrieved from https://submit-etda.libraries.psu.edu/catalog/8896

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

Chicago Manual of Style (16th Edition):

Hester II, David Keith. “PART I. EXTENDING ALLENYL AZIDE CYCLOADDITION CHEMISTRY: PHOTOCHEMISTRY AND CU(I) MEDIATION. PART II. EFFORTS TOWARD THE TOTAL SYNTHESIS OF (-)-KINAMYCIN F. PART III. EFFECT OF STRENGTH AND SYMMETRY OF HYDROGEN BONDS ON QUINONE REDUCTION POTENTIAL.” 2008. Thesis, Penn State University. Accessed November 29, 2020. https://submit-etda.libraries.psu.edu/catalog/8896.

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

MLA Handbook (7th Edition):

Hester II, David Keith. “PART I. EXTENDING ALLENYL AZIDE CYCLOADDITION CHEMISTRY: PHOTOCHEMISTRY AND CU(I) MEDIATION. PART II. EFFORTS TOWARD THE TOTAL SYNTHESIS OF (-)-KINAMYCIN F. PART III. EFFECT OF STRENGTH AND SYMMETRY OF HYDROGEN BONDS ON QUINONE REDUCTION POTENTIAL.” 2008. Web. 29 Nov 2020.

Vancouver:

Hester II DK. PART I. EXTENDING ALLENYL AZIDE CYCLOADDITION CHEMISTRY: PHOTOCHEMISTRY AND CU(I) MEDIATION. PART II. EFFORTS TOWARD THE TOTAL SYNTHESIS OF (-)-KINAMYCIN F. PART III. EFFECT OF STRENGTH AND SYMMETRY OF HYDROGEN BONDS ON QUINONE REDUCTION POTENTIAL. [Internet] [Thesis]. Penn State University; 2008. [cited 2020 Nov 29]. Available from: https://submit-etda.libraries.psu.edu/catalog/8896.

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

Council of Science Editors:

Hester II DK. PART I. EXTENDING ALLENYL AZIDE CYCLOADDITION CHEMISTRY: PHOTOCHEMISTRY AND CU(I) MEDIATION. PART II. EFFORTS TOWARD THE TOTAL SYNTHESIS OF (-)-KINAMYCIN F. PART III. EFFECT OF STRENGTH AND SYMMETRY OF HYDROGEN BONDS ON QUINONE REDUCTION POTENTIAL. [Thesis]. Penn State University; 2008. Available from: https://submit-etda.libraries.psu.edu/catalog/8896

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

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