A Convenient, Large Scale Synthesis of trans-(+)-Sobrerol

Abstract

A convenient and highly efficient synthesis of optically pure trans-(+)-sobrerol (1), starting from methyl 3,5-dihydroxy-4-methyl benzoate 2 in 8 steps with overall yield 26%, is reported. The key intermediate 4 is prepared in remarkably high yield by selectively esterification of 3 using lipase as catalyst. A critical step to stereoselectively inverse the configuration of 7 is realized under Mistunobu conditions.

Acknowledgments

Q.W. thanks Professor M. Vandewalle (University of Gent, Belgium), in whose laboratory part of this work was initiated.