Optical resolution of dl-threo-2-(2,4-difluorophenyl)-2-[1-(methylthio)ethyl]oxirane: Its application to the synthesis of SM-9164, a biologically active enantiomer of antifungal agent SM-8668

Article abstract of DOI:10.1246/bcsj.68.3591

A racemate of threo-2-(2,4-difluorophenyl)-2-[1-(methylthio)ethyl]oxirane was separated into two enantiomers by reaction with a chiral carboxylic acid, followed by separation of the resultant diastereomers, hydrolysis of the ester, and dehydration of the 1,2-diol to the oxirane. This new optical resolution method was applied to the synthesis of SM-9164, a biologically active enantiomer of antifungal agent SM-8668. Thus, the optically active isomer of SM-8668 was prepared efficiently in eight steps from m-difluorobenzene.