Date of Award

Spring 2019

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

School

Mathematics and Natural Sciences

Committee Chair

Julie Pigza

Committee Chair School

Mathematics and Natural Sciences

Committee Member 2

Matthew Donahue

Committee Member 2 School

Mathematics and Natural Sciences

Committee Member 3

Douglas Masterson

Committee Member 3 School

Mathematics and Natural Sciences

Committee Member 4

Gopinath Subramanian

Committee Member 4 School

Polymer Science and Engineering

Committee Member 5

Paige Buchanan

Abstract

Natural products are widely used in the pharmaceutical industry, in agriculture, and as specialty chemicals. Methodology development focuses on optimizing the key organic reactions to access these natural products while trying to limit the overall number of synthetic steps. Key bond forming strategies are sought to provide new ways to address carbon-carbon or carbon-heteroatom bonds. The advancement of new asymmetric reactions to generate enantiopure products from achiral starting materials is a vital area of research. The objectives addressed in this dissertation include: 1) the development of a general reductive conversion of esters to ethers with a broad substrate scope accessing both aromatic and non-aromatic esters as well as accessing challenging α-substituted ethers, 2) the development of synthetic strategies for the preparation of trisubstituted biaryl quinoline scaffolds and subsequent derivatization to produce a library of heterocyclic substrates for the inhibition of HIV-1 integrase, and 3) the use of organocatalysis to explore new reactions and, through π-π and H-π bonding interactions between catalysts and substrates, to result in improved enantioselection as compared to transition-metal catalyzed reactions.

ORCID ID

0000-0003-0809-3013

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