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18-oxo-ETE was synthesized via the corresponding tetraacetylenic precursor, which was prepared by cross-coupling of three key synthons: methyl 5-hexynoate, the bisfunctional C 7 -C 13 fragment-7-bromo-2,5-heptadiyne-1-ol and rac-3-(benzoyloxy)hept-6-yn. The carbonyl function was introduced at the last synthesis step. 19-oxo-ETE was synthesized by coupling of acid anhydride, prepared...
18-Iodooctadeca-(8Z,11Z)-dienoic acid (7) was synthesized in five steps starting from methyl 10-bromodec-7-ynoate (2) in an overall yield of 53%. The synthetic procedure involves Cu(I)-catalyzed cross-coupling of propargylic bromide 2 with 7-octyn-1-ol (3), followed by hydrogenation of the coupling product 4 to Z,Z-diene 5 on Lindlar's catalyst and subsequent substitution of the OH– group of 5 with...
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