Stereoselective formation of a beta-lactam fused oxathiazepin: A synthetic approach to eudistomins

摘要

A synthetic approach to eudistomin via a beta-lactam fused bicyclic oxathiazepin intermediate is described. A beta-lactam fused oxathiazepin derivative was synthesized by intramolecular 7-membered oxime ether formation and subsequent face-selective reduction of the C-N double bond. A fully functionalized ortho-alkenylphenylthioanilide bearing oxathiazepin ring was then prepared and construction of the indole skeleton under several radical-mediated conditions was examined. [References: 24]