4.8 Article

Total Synthesis of (-)-Lepistine

Journal

ORGANIC LETTERS
Volume 16, Issue 11, Pages 2862-2864

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5010033

Keywords

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Funding

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

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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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