Issue 24, 2022

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
24 Sep 2022
Accepted
25 Oct 2022
First published
26 Oct 2022

Org. Chem. Front., 2022,9, 6849-6852

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

T. Mashiko, E. Nagata, H. Sakate, S. Kamo and K. Sugita, Org. Chem. Front., 2022, 9, 6849 DOI: 10.1039/D2QO01525K

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