A Synthesis of (Z)-Octadec-9-enedioic Acid

Abstract

The monomethyl ester of azelaic acid was transformed into two fragments, namely[8-(methoxy -carbonyl)octyl]triphenylphosphonium bromide and methyl 9-oxononanoate. A Wittig reaction between these two fragments produced dimethyl(Z)-octadec-9-enedioate and subsequent hydrolysis gave the title diacid.Interestingly, the same diacid was available directly from oleic acid in a published procedure which utilized a mutant strain of Candida tropicalis. © 1995 ASEG.