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Title Innovative approaches to carbocyclic and heterocyclic compounds using strained carbocycles
Publication Date
Date Accessioned
Degree PhD
Discipline/Department Chemistry and Biochemistry
Degree Level doctoral
University/Publisher Georgia Tech
Abstract Natural products and small molecules play a major role in drug development. However, using natural products as a source of medicine comes with many challenges, such as lack of natural abundance and difficulty in isolation. Consequently, synthetic organic chemistry is a solution in order to access these compounds in usable quantities. However, synthetic chemisty comes with its own challenges such as efficiency, chemoselectivity, stereoselectivity and enantioselectivity. Therefore, synthetic tools that addresses these challenges are required solve these limitations. This thesis discusses new methodologies using strained carbocycles (cyclopropanes and cyclopropenes) as the reactive subunit for the construction of different carbocyclic and heterocyclic compounds. The homo-Nazarov cyclization of alkenyl and heteroaryl cyclopropyl ketones was used in order to construct cyclohexenones, cyclohexenols, heteroaryl ring-fused cyclohexenones, dihydrofurans, furans and furanones in a mild and efficient manner. Benzofused heteroaromatic compounds were achieved via the Lewis acid-catalyzed cycloisomerization of cyclopropene-3,3-dicarbonyls and furan-3-carboxylates. These heteroaromatic compounds can be applied to medicinal chemistry and material science.
Subjects/Keywords Furans; Carbocycles; Heterocycles; Cyclopropane; Cyclopropene; Diazo; Drug development; Pharmacognosy
Contributors [email protected] (Committee Chair); charles liotta (Committee Member); christoph fahrni (Committee Member); david collard (Committee Member); julia kubanek (Committee Member)
Country of Publication us
Record ID handle:1853/47542
Repository gatech
Date Indexed 2020-05-13
Issued Date 2013-01-14 00:00:00
Note [degree] PhD; [advisor] Committee Chair: [email protected]; Committee Member: charles liotta; Committee Member: christoph fahrni; Committee Member: david collard; Committee Member: julia kubanek;

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