Total synthesis of methyl 14-hydroxy-(all-cis)-5,8,11-tetradecatrienoate: A useful intermediate for the synthesis of arachidonic acid analogues

Article abstract of DOI:10.1016/S0040-4039(97)10607-4

The first total synthesis of methyl 14-hydroxy-(all-cis)-5,8,11-tetradecatrienoate (1a) was accomplished in 11 steps with an overall yield of 14%. Major sequences involve Cu(I) catalyzed propargylic substitution of propargyl bromide 5 by 3-butyn-1-ol, followed by partial reduction of the diyne 6 to the cis,cis-diene 7, and Wittig reaction of the phosphonium iodide 9 with aldehyde 11 to the all-cis skipped triene 10.