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Synlett 1992; 1992(11): 889-890
DOI: 10.1055/s-1992-21529
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Stereoselective Synthesis of the trans 2,4-Disubstituted Butyrolactone Moiety of Annonaceous Acetogenins

Philippe Bertrand* , Jean-Pierre Gesson
  • *Laboratoire de Chimie XII, URA 1468, 40, Avenue du Recteur Pineau, F-86022 Poitiers, France
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Publication Date:
08 March 2002 (online)

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The stereoselective preparation of the trans 2-alkyl-4-acetonylbutyrolactone moiety present in some bioactive mono or bis-tetrahydrofuran acetogenins has been carried out from glycidol tosylate using two consecutive alkylations. The formation of a methyl pyranoside from the intermediate mixture of epimeric cyano alcohols allows control of the relative 1,3-configurations before lactonization.

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