Letter

Total Synthesis of (−)-Lepistine

Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan
Org. Lett., 2014, 16 (11), pp 2862–2864
DOI: 10.1021/ol5010033
Publication Date (Web): May 9, 2014
Copyright © 2014 American Chemical Society

Abstract

Abstract Image

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.

Supporting Information


Experimental details and spectroscopic data. This material is available free of charge via the Internet at http://pubs.acs.org.

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Article Views: 4,620 Times
Received 5 April 2014
Published online 9 May 2014
Published in print 6 June 2014
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