Two geometrical isomers of linoleic acid: Improved total syntheses

The total syntheses of 9(Z),12(E)- and 9(E),12(Z)-octadecadienoic acids have been carried out. A useful intermediate in both syntheses, 8-bromo-octanoic acid, recently has become available from commercial sources. This compound has been used to expedite the preparation of these isomers. The remaining carbon atoms were derived from propargyl alcohol along with either 1-heptyne or acetylene and 1-bromopentane. Because the overall yield for each sequence was roughly 15% and there were no extraordinary reaction conditions in any of the synthetic steps, the compounds could be prepared readily in multiple gram quantities. The syntheses of the two compounds were supported by data from a variety of spectroscopic techniques.