Three approaches for the synthesis of octadecadienoic acids with conjugated double bond systems are presented: synthesis of (10Z, 12Z)-octadecadienoic acid via an enyne-substructure; the use of an educt with a conjugated double bond system for the synthesis of (10E, 12E)-octadecadienoic acid; and the Suzuki cross coupling for the synthesis of (7E,9Z)-octadecadienoic acid.
(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.
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