☆ 4.8 Article

Total Synthesis of (-)-Lepistine

ORGANIC LETTERS (2014)

Journal

ORGANIC LETTERS

Volume 16, Issue 11, Pages 2862-2864

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/ol5010033

Keywords

-

Categories

Chemistry, Organic

Funding

JSPS KAKENHI [20002004, 25221301]
Platform for Drug Discovery, Informatics, and Structural Life Science (MEXT)
Sumitomo Foundation
Tokyo Biochemical Research Foundation

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Abstract

The first total synthesis of (-)-lepistine has been accomplished in 11 steps from (S)-glycidol. The synthesis features construction of the 10-membered ring via an intramolecular epoxide opening by nosylamide, regioselective dehydration to form an enol ether, and construction of the aminal moiety induced by cleavage of the nosyl groups.

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