Stereoselective syntheses of (+)- and (−)-terconazole

Abstract The recently described cis- benzoates (2R,4R)- and (2S,4S)- 2 were transformed into (+)- and (−)-terconazole, respectively, by reaction with 1 H -1,2,4-triazole followed by hydrolysis to give alcohols (+)- and (−)-3 which were mesylated and reacted with phenol 5 . The ee's of (+)- and (−)-terconazole determined by HPLC on the CSP Chiralcel OD-H were > 99%.