Class Year

2018

Date

4-18-2018

Document Type

Thesis

Distinguished Thesis

Yes

Degree Name

Bachelor of Arts (BA)

Department or Program

Chemistry

First Advisor

Paul Gladen

Second Advisor

Jason A. Cody

Third Advisor

Rebecca S. Graff

Abstract

Two independent projects oriented to synthesize naturally occurring compounds: a model of citreamicin θ A, and xanthocercin A with methoxy-butesuperin B. Citreamicin θ A was isolated from marine-derived bacteria Streptomyces caelestis and has been reported to possess antibacterial activity against multi-drug resistant Staph.aureus(MRSA). The key reactions in the multi-step synthesis of the citreamicin model compound involved a Sonogashira coupling and Diels-Aldercycloaddition. Xanthocercin A and methoxy-butesuperin B were isolated in a mixture with other chemical compounds from leadplant, Amorpha canescens. Due to the lack of material from natural sources, the structure and pharmaceutical properties of the compound can be confirmed only with the presence of an appropriate amount of the pure material. As part of ongoing efforts to fully verify the structure of the isolated natural products, we prepared a synthetic sample of both xanthocercin A and methoxy-butesuperin B

Language

English


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