Synlett 2012; 23(12): 1832-1834
DOI: 10.1055/s-0031-1290407
letter
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Total Synthesis of ent-Tetrahydrolipstatin from an Epoxy Alkenol

Hyemi Kim
Department of Chemistry, Yonsei University, Seoul 120-749, Korea, Fax: +82(2)3647050   Email: jstae@yonsei.ac.kr
,
Kyeonghwan Choi
Department of Chemistry, Yonsei University, Seoul 120-749, Korea, Fax: +82(2)3647050   Email: jstae@yonsei.ac.kr
,
Jinsung Tae*
Department of Chemistry, Yonsei University, Seoul 120-749, Korea, Fax: +82(2)3647050   Email: jstae@yonsei.ac.kr
› Author Affiliations
Further Information

Publication History

Received: 12 April 2012

Accepted after revision: 07 May 2012

Publication Date:
04 July 2012 (online)


Abstract

A highly efficient asymmetric total synthesis of ent-­tetrahydrolipstatin (THL) was accomplished from the known epoxy alkenol. The β-lactone portion of THL was synthesized by the epoxide opening with cyanide and stereoselective enolate alkylation method. The side chain was introduced by cross metathesis of the alkene part with 1-decene. Coupling with a protected leucine completed the synthesis of ent-tetrahydrolipstatin.

Supporting Information