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Article

A Concise Synthesis of (+)-Cerulenin from a Chiral Oxiranyllithium

Supporting Info

Neelakandha S. Mani and Craig A. Townsend*

Department of Chemistry, The Johns Hopkins University, Baltimore, Maryland 21218

J. Org. Chem., 1997, 62 (3), pp 636–640

DOI: 10.1021/jo9618177

Publication Date (Web): February 7, 1997

Address correspondence to this author: Department of Chemistry, The Johns Hopkins University, Charles & 34th Streets, Baltimore, MD 21218. tel: 410-516-7444. fax: 410-516-8420. email: Townsend@ jhunix.hcf.jhu.edu.

Abstract

(+)-Cerulenin, a potent fungal inactivator of fatty acid synthases, has been prepared in optically pure form by a sequence involving reaction of a chiral oxiranyllithium with (4E,7E)-nonadienal. Synthesis of the former takes advantage of a particularly favorable Sharpless epoxidation and metalation to a configurationally stable organolithium, while the latter is available in quantity by a direct and improved route.

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