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.