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

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.

Automated summary

The first total synthesis of (+)-ent-vetiverianine A, which has a 5/6/6-fused tricyclic structure, is described in this study. Key reactions such as Lewis acid-mediated cyclization, Mukaiyama hydration, enantioselective Shi epoxidation, Birch reduction, and other transformations were utilized, leading to an enantioselective access to (+)-ent-vetiverianine A in 14 steps with an overall yield of 12%.