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

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.