Total synthesis of (+)-ent-vetiverianine a via Lewis acid-mediated cyclization

Abstract

Herein, we describe the first total synthesis of (+)-ent-vetiverianine A, which exhibits a 5/6/6-fused tricyclic structure. The key reactions, including Lewis acid-mediated cyclization, Mukaiyama hydration, enantioselective Shi epoxidation, Birch reduction, and other effective transformations, enabled enantioselective access to (+)-ent-vetiverianine A with the longest linear sequence of 14 steps, and in 12% overall yield.