Abstract: A novel and highly efficient synthesis of optically pure trans-(+)-sobrerol,starting from methyl 3,5-dihydroxy-4-methyl benzoate(2) in 7 steps with overall yield 27%,was reported. The key intermediate(+)-5 was prepared in remarkably high yield by lipase__catalyzed asymmetrization of 4. A critical step to stereoselectively inverse the configuration of(+)-6 was realized under Mistunobu conditions. The structures of all the compounds were confirmed by IR,MS and NMR spectra.

Key words: trans-(+)-Sobrerol, Terpinediol, Optical purity