A Facile and Efficient Method for the Synthesis of Labeled and Unlabeled Very Long Chain Polyunsaturated Fatty Acids

Abstract Several methods are available for elongation of fatty acid acyl chains. The present paper describes adaptation to the field a previously published protocol manganese‐based Wurtz type coupling alkyl bromides. 22‐Bromo‐3( Z ),6( ),9( ),12( ),15( ),18( )‐docosahexaene, easily prepared from 4( ),7( ),10( ),13( ),16( ),19( )‐docosahexaenoic acid, was coupled homologous ω‐bromoesters by stirring 4 hours at 40°C in presence manganese powder, nickel catalyst and terpyridine. This afforded yields 70–75% series ω3‐hexaenoates chain lengths 32–40 carbons. corresponding acids >98% purity were obtained following saponification final purification. By using methyl [2,2,3,3,4,4‐ 2 H 6 ]10‐bromodecanoate as partner it possible prepare very long isotopically labeled form, i.e., ]14( ),17( ),20( ),23( ),26( ),29( )‐dotriacontahexaenoic acid. Also monounsaturated 15( )‐octadecenoic )‐tetracosenoic Very have been isolated retina other tissues biological relevance. methodology described will assist further analytical studies this field.