Asymmetric synthesis of 5,7-O-dimethyleucomols via enantioselective oxidation of enol phosphates

Abstract

The asymmetric synthesis of some derivatives of the homoisoflavone class, (S)-(−)- and (R)-(+)-5,7-O-dimethyleucomols, and (−)-homoisoflavone epoxide, based on the asymmetric oxidation of the corresponding enol phosphates, is described. The influence of electronic and steric effects of the enol phosphate substituents on the facial stereoselectivity of oxidation was observed.