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A concise enantioselective synthesis of the chlorosulfolipid malhamensilipin A.

ABSTRACT: The first enantioselective synthesis of a member of the chlorosulfolipid family of natural products is reported. All of the polar substituents of malhamensilipin A are introduced with high stereoselectivity, and the unique (E)-chlorovinyl sulfate is created by a chemo-, regio-, and stereoselective E2 elimination of HCl in a reaction that likely has a counterpart in the biosynthesis of this fascinating natural product.

SUBMITTER: Bedke DK

PROVIDER: S-EPMC2830791 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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A concise enantioselective synthesis of the chlorosulfolipid malhamensilipin A.

Bedke D Karl DK Shibuya Grant M GM Pereira Alban R AR Gerwick William H WH Vanderwal Christopher D CD

Journal of the American Chemical Society 20100301 8

The first enantioselective synthesis of a member of the chlorosulfolipid family of natural products is reported. All of the polar substituents of malhamensilipin A are introduced with high stereoselectivity, and the unique (E)-chlorovinyl sulfate is created by a chemo-, regio-, and stereoselective E2 elimination of HCl in a reaction that likely has a counterpart in the biosynthesis of this fascinating natural product. ...[more]

PMID: 20141139

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