Synthesis of (Z,Z)-octadeca-10,12-dienoic acid

Abstract

(Z,Z)-Octadeca-10,12-dienoic acid was synthesised by coupling (Z)-1-bromohept-1-ene with protected undec-10-yne-1-ol. Stereoselective hydrogenation of the triple bond of the obtained enyne-system followed by deprotection yielded (Z,ZZ)-octadeca-10,12-dienol. The latter can be easily oxidized to the corresponding acid.