Total synthesis of (-)-bitungolide F.

J Org Chem

Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China.

Published: April 2009

An efficient total synthesis of (-)-bitungolide F (6) in 17 steps and 20.1% yield is described herein. Key steps involve a Myers asymmetric alkylation to introduce the C6 methyl with proper stereochemistry, a Claisen-like cyclization to construct the alpha,beta-unsaturated delta-lactone and a Julia-Kocienski olefination to assemble the conjugated diene moiety.

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http://dx.doi.org/10.1021/jo9000146DOI Listing

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