A new route for the synthesis of the optically active antifungal azole TAK-187, 2-[(1R, 2R)-2-(2, 4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-4-[4-(2, 2, 3, 3-tetrafluoropropoxy)phenyl]-3(2H, 4H)-1, 2, 4-triazolone, was established. The key synthetic intermediate, 2-[(1R)-2-(2, 4-difluorophenyl)-2-oxo-1-methylethyl]-4-[4-(2, 2, 3, 3-tetrafluoropropoxy)phenyl]-3(2H, 4H)-1, 2, 4-triazolone (8), was prepared starting from the esters (11a, b) of (S)-lactic acid in a stereocontrolled manner. This optically active propiophenone derivative 8 was converted to the one carbon-elongated (1R, 2S)-diol 7, which was then reacted with 1H-1, 2, 4-triazole to yield TAK-187. This newly developed route was applied to the synthesis of the analogs (25a, b-28a, b)containing an imidazolone or imidazolidinone nucleus.