Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 24, Pages 6849-6852Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01525k
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Funding
- JSPS KAKENHI [JP16K08180, JP19K06981, JP21K14797]
- Pharmaceutical Society of Japan
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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%.
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.
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