Date of Award

2020

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Graduate Group

Chemistry

First Advisor

Jeffrey D. Winkler

Abstract

The natural product bruceantin has long been studied for both its biological activity and its structural complexity. Attempts to synthesize more stable analogs for the development of inhibitors of γ-herpesviruses associated lymphomas are presented. In addition, a new method for the synthesis of the bridged bicyclic core structure of bruceantin using a homologous Pauson-Khand reaction of a bicyclo[2.1.0]pentane substrate is presented. Simple azabicyclo[2.1.0]pentane substrates were synthesized and studied for proof of concept of this approach in both rhodium- and palladium-catalyzed reactions. The palladium-mediated reaction led to the formation of enantiopure spirocyclic heterocycles.

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Chemistry Commons

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