Preparation of 15-hydroxypentadecanoic acid by means of condensation reaction via β-ketosulfoxide

Abstract

Basic condensation of 1,12-dodecanolide with methylsulflnylcarbanion (DMSO−) gives a β-keto-sulfoxide 2 which is ethoxycarbonylmethylated and the product is converted to 15-hydroxypentadecanoic acid (6) in a 46% overall yield based on the lactone. Another β-ketosulfoxide 9 is prepared by condensation of methyl 10-undecenoate with DMSO− and is subjected to the Michael condensation with methyl acrylate. Treatment of the adduct gives 14-pentadecenoic acid (13) in a 38% overall yield based on the undecenoate.