Asymmetric synthesis of syn and anti 1,2-diols from diethyl oxalate using the stereoselective sulfoxide directed reduction of 1,2-diketone derivatives

A new chiral Wittig reagent, a beta-keto-gamma-(S)-hydroxy-delta-(R)-p-toly lsulfinyl phosphonate, readily made from ethyl oxalate and stereoselective sulfoxide mediated reduction of the resulting beta-ketosulfoxide, was used to prepare enantiomerically pure syn and anti 1,2-diols. This method was ap plied to the enantioselective synthesis of two acetogenin derivatives, (-)- (R,R)-muricatacin and its epimer (-)-(R,S)-epi-muricatacin. (C) 1999 Elsevi er Science Ltd. All rights reserved.