ChemInform Abstract: Enantioselective Biocatalytic Synthesis of (S)‐Monastrol.

Abstract

Enantioselective Biocatalytic Synthesis of (S)-Monastrol. -The first enantioselective biocatalytic synthesis of (S)-monastrol (II) is developed via an unexpected and unusual enzymatic pathway. Whereas attempts for a direct hydrolysis of racemic monastrol are not successful, formation of racemic O-butanoyl monastrol and subsequent enantioselective hydrolysis furnishes O-butanoyl (S)-monastrol with 97 % enantiomeric excess. Subsequent chemoselective cleavage in the presence of another lipase yields the targeted compound in high yield and with a high enantiomeric excess. The method seems to be suitable for other types of racemic phenol esters. -(BLASCO, M. A.; THUMANN, S.; WITTMANN, J.; GIANNIS, A.; GROEGER*, H.; Bioorg. Med.