ABSTRACT

The need for the laboratory synthesis of unsaturated fatty acids arises when these acids do not occur naturally, are found only at low level in obscure sources, or when an isotopically labelled sample is required. Many synthetic procedures have been employed and those based on the reactivity of acetylene (ethyne) and its derivatives have been widely exploited. The first synthesis of an unsaturated C18 fatty acid, oleic [18:1(9c)], was recorded in 1934 (Noller and Bannerot, 1934). With the emergence of the methylene-interrupted (skipped) polyenoic fatty acids as a physiologically important group of fatty acids, extensive use of the acetylenic route and later via the Wittig reaction (first applied to fatty acid synthesis by Bergelson and Shemyakin (1964)), led to the production of numerous polyunsaturated fatty acid isomers for physical, chemical, and biological studies. Linoleic acid [18:2 (9c,12c)] (an essential fatty acid) was first synthesised in 1950 (Raphael and Sondheimer, 1950).