Stereoselection in the Prins-Pinacol Synthesis of 2,2-Disubstituted 4-Acyltetrahydrofurans. Enantioselective Synthesis of (−)-Citreoviral

Abstract

[reaction: see text] The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the alpha-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.