Concise Total Synthesis and Stereochemical Revision of all (-)-Trigonoliimines

Abstract

The concise and enantioselective total syntheses of (-)-trigonoliimines A, B, and C are described. Our unified strategy to all three natural products is based on asymmetric oxidation and reorganization of a single bistryptamine, a sequence of transformations with possible biogenetic relevance. We revise the absolute stereo chemistry of (-)-trigonoliimines A, B, and C.