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Epidithiodioxopiperazines: synthetic studies of (+)-chetomin and (-)-sporidesmin A

Date

2012

Authors

Welch, Timothy R., author
Williams, Robert M., advisor
Rovis, Tomislav, committee member
Wood, John L., committee member
Ackerson, Chris, committee member
Thamm, Douglas H., committee member

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Abstract

This dissertation documents efforts toward the asymmetric total syntheses of the natural products (+)-chetomin and (-)-sporidesmin A. Synthetic methods have been developed to efficiently construct the dioxopiperazine core of both molecules. Additionally, a simple epidithiodioxopiperazine has been synthesized to demonstrate a general method for the addition of a sulfur bridge to a dioxopiperazine ring. The work described herein, while not totally successful, provides a basis for future completion of the asymmetric total syntheses of these two epidithiodioxopiperazines and other related fungal metabolites.

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