Synthesis of γ-lactones by desymmetrization. A synthesis of (-)-muricatacin

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Abstract

A short synthesis of the natural potent cytotoxic agent (-)-muricatacin 1 and related unsaturated lactones from a versatile common intermediate, dienedioate 2, derived from d-mannitol or tartaric acid, is described. The strategy depends upon the desymmetrization of 7 by dihydroxylation and elaboration of the hydroxy alkyl sidechain. A route to unsaturated lactones is also described using a cis selective Wittig reaction. Since the enantiomers of 2 are available from the corresponding tartaric acids, this method provides access to both enantiomers of the described compounds and a wide range of derivatives.

Original languageEnglish
Pages (from-to)396-399
Number of pages4
JournalTetrahedron
Volume65
Issue number1
DOIs
Publication statusPublished - 3 Jan 2009

Keywords

  • Desymmetrization
  • Enantioselective
  • Enoate
  • γ-Lactones

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