Synthesis of (S)-(+)-parasorbic acid and (S)-(+)-2-tridecanol acetate: Bakers' yeast reductions of γ and δ ketosulfones

Abstract

The enantioselective reduction of 4-(p-toluenesulfonyl) butane-2-one and 5-(p-toluenesulfonyl) pentane-2-one with bakers' yeast gave the corresponding (S) alcohols in high optical purities and moderately good yields. The alcohol 2a was converted to (S)(+)parasorbic acid ( 4), while 2b was used for the preparation of (S)(+)-2-tridecanol acetate ( 7), using short synthetic sequences.