Stereoselective Synthesis of the trans 2,4-Disubstituted Butyrolactone Moiety of Annonaceous Acetogenins
- 1 January 1992
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1992 (11) , 889-890
- https://doi.org/10.1055/s-1992-21529
Abstract
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.Keywords
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