出版社：American Society for Biochemistry and Molecular Biology
摘要：A general procedure for the synthesis of 2- trans polyenoic fatty acids and of dl -3-hydroxypolyenoic acids is described. The 2- trans acids are prepared by LiAlH4 reduction of a suitable polyenoic fatty acid ester to the alcohol, formation of the tosylate, oxidation to the aldehyde, and Doebner condensation of the latter with malonic acid. The 3-hydroxy acids are obtained by reaction of the acyl chloride of a suitable polyenoic acid with the sodium enolate of methyl acetoacetate and sodium methoxide to give the 3-keto ester, the keto group of which is reduced with sodium borohydride to the alcohol. These procedures were applied to the synthesis of eicosa-2- trans -8,11,14-all cis -tetraenoic acid-3-14C and dl -3-hydroxy eicosa-8,11,14-trienoic acid-3-14C.
