Synthesis of All Four Possible Stereoisomers of 1-Phenyl-2, 3-butanediol and Both Enantiomers of 3-Hydroxy-4-phenyl-2-butanone to Determine the Absolute Configuration of the Natural Constituents

Abstract

Enantioselective syntheses of all the possible stereoisomers of 1-phenyl-2, 3-butanediol (erythro isomer 1 and threo isomer 2) and of 3-hydroxy-4-phenyl-2-butanone 3, the odor components of wisteria flowers, was accomplished via Sharpless asymmetric epoxydation. The absolute configurations of 1-3 were determined by an HPLC analysis of the corresponding MTPA esters of synthetic samples.