A novel synthesis of 3(R)-HETE, 3(R)-HTDE and enzymatic synthesis of 3(R),15(S)-DiHETE

3(R)-HETE and 3(R)-HTDE were prepared by cross-coupling of methyl 3(R)-hydroxyhex-5-ynoate either with 1-bromo-2,5,8-tetradecatriyne or 1-bromo-2-octyne followed by catalytic hydrogenation of the skipped triple bonds formed using Lindlarʹs catalyst. Enzymatic synthesis of 3(R),15(S)-DiHETE was accomplished by soybean LOX-1 using 3(R)-HETE as a substrate.