The synthesis of 1-14C-arachidonate and 3-14C-docosa-7,10,13,16-tetraenoate

Methyl 1-¹⁴C-arachidonate was prepared by coupling 1-bromotetradeca-2,5,8-triyne with 4-pentyn-1-ol to yield nonadeca-4,7,10,13-tetrayn-1-ol. This compound was reduced with Lindlars catalyst. The resulting alcohol was converted to the mesylate and then to the nitrile which in turn was converted to methyl 1-¹⁴C-arachidonate by hydrolysis with anhydrous HCl in methanol. The methyl 1-¹⁴C-arachidonate was reduced to the alcohol with LiA1H₄ and converted to the mesylate which in turn was treated with diethyl malonate. Following saponification and decarboxylation 3-¹⁴C-docosa-7,10,13,16-tetraenoic acid was obtained. Presented at the AOCS-ISF Meeting, Chicago, September 1970.