Synthesis of Unsaturated Lipid Mediators having Anti-inflammatory Actions

omega-3 Fatty acids such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) produces hydroxylated metabolites that mediate resolution of inflammation process. Such metabolites are divided to E-series and D-series resolvins, protectins, and maresins. In addition to the hydroxyl groups, these metabolites involve conjugated diene, triene, and/or tetraene possessing one cis olefin. These conjugated olefins with hydroxyl groups are chemically unstable, so that usable reactions/reagents are limited at the last stage of the synthesis. This review summarizes synthesis of resolvins El, E2, D5, protectin D1, and maresin 1, focusing on the methods that construct stereoselectively the conjugated olefins and alcoholic carbons of these metabolites.