A short synthesis of (-)-(4R,5S)-sitophilure using the regio- And stereoselective reduction of 3-acyltetrahydrothiopyran-4-ones with baker's yeast

Article abstract of DOI:10.1016/S0040-4039(00)61147-4

Bakers' yeast reduction of 3-acyltetrahydrothiopyran-4-ones is regio- and enantioselective, yielding predominantly (3R,4S)-3-acyl-4- hydroxytetrahydrothiopyranes with high optical purity. This reduction method coupled with the Raney-nickel desulfurization provides a ready access to the rice and maize weevils aggregation pheromone, (-)-(4R,5S)-sitophilure, in high optical purity.