Lipase-mediated asymmetric acetylation of prochiral diols directed towards total syntheses of biologically active molecules

Abstract

Lipase mediated asymmetric acetylation of σ-symmetrical 2-aryl-1,3-propanediols ( 1a–f), which were prepared conveniently via sequential Heck coupling between ( 5a–f) and ( 6), ozonolysis and reductive workup, provided the enantiomerically enriched monoacetates ( 2a–f) in good chemical and optical yields. These monoacetates ( 2a–f) were successfully converted into the biologically and pharmacologically interesting molecules, Baclofen ( 10), ar-turmerone ( 13), α-cuparenone ( 19), ent-aflatoxin B 2 ( 24), ibuprofen ( 26), naproxen ( 28), and indolmycin ( 32) as optically active forms, respectively.