Stereoselective synthesis of antifungal agent threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl )-2-butanol (SM-8668)

Article abstract of DOI:10.1246/bcsj.67.1427

The stereoselective synthesis of antifungal agent threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl )-2-butanol (SM-8668) is described. The key step is the selective synthesis of intermediate threo-2-(2,4-difluorophenyl)-2-(1-substituted ethyl)oxirane. threo-2-(2,4-difluorophenyl)-2-(1-methylthioethyl)oxirane was synthesized threo-selectively by the reaction of 1-(2,4-difluorophenyl)-2-methylthio-1-propanone with dimethyloxosulfonium methylide in a heterogeneous media consisting of a hydrophobic solvent and aqueous alkaline solution.