Synthesis of three isomers of linoleic acid

Thesis (Ph.D.)--Boston UniversityThree skipped unsaturated fatty acids, 8,11-octadecadienoic acid, 10,13-octadecadienoic acid and 11,14-octadecadienoic acid have been synthesized via skipped acetylenic intermediates. Coupling an w-chloroacetylenic Grignard derivative I with a propargylic bromide II in tetrahydrofuran in the presence of cuprous chloride catalyst yielded a 1-chloroheptadecadiyne III, which was reduced stereospecifically and selectively to the di-cis-1-chloroheptadecadiene IV by two treatments with diisobutylaluminum hydride. The diene IV was converted to the Grignard reagent which upon carbonation and acidification gave the octadecadienoic acid V[TRUNCATED