Synthesis of a highly fluorinated fatty acid analog

A five-step synthesis of Z-11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-heptadecafluoro-octadec-8-enoic acid is reported, starting from 1,8-octanediol and 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iododecane. The key step is a Wittig reaction to form the C8–C9 double bond with a Z:E isomeric ratio of 10:1. The route should be generally applicable to the synthesis of highly fluorinated monounsaturated fatty acids.