OPTICALLY-ACTIVE ANTIFUNGAL AZOLES .4. SYNTHESIS AND ANTIFUNGAL ACTIVITY OF (2R,3R)-3-AZOLYL-2-(SUBSTITUTED PHENYL)-1-(1H-1,2,4-TRIAZOL-1-YL)-2-BUTANOLS

(2R,3R)-3-Azolyl-2-(substituted phenyl)-1-(1H-1,2,4-triazol-1-yl)-2-bu tanols (III) were prepared from (2R,3S)-3-methyl-2-(substituted phenyl )-2-(1H-1,2,4-triazol-1-yl)methyloxiranes (21a-f) by a ring-opening re action with 1H-1,2,3-triazole and 1H-tetrazole and evaluated for antif ungal activity against Candida albicans in vitro and in vivo. The opti cally active oxiranes (21a-f), which serve as the key synthetic interm ediates, were synthesized from 6-tetrahydro-2H-pyran-2-yl)oxypropanoyl ]morpholine (24) and substituted phenylmagnesium bromide (23) via six steps in a stereocontrolled manner. The 3-(1H-1,2,3,-triazol-1-yl)-(II Ia) and 3-(2H-2-tetrazolyl)-2-butanol (IIId) derivatives showed strong protective effects against candidosis in mice.