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Maresin-L1 (14 S ,22-dihydroxy-docosa-4 Z ,7 Z ,10 Z ,12 E ,16 Z ,19 Z -hexaenoic acid) and maresin-L2 (14 R ,22-dihydroxy-docosa-4 Z ,7 Z ,10 Z ,12 E ,16 Z ,19 Z -hexaenoic acid) were chemically synthesized. They were identical to activated macrophage produced counterparts and their total synthesis was highly Stereoselective, as revealed by chiral LC-UV-MS/MS analysis. The synthesis involved the following steps: (1) kinetic resolution of a racemic allylic alcohol by the asymmetric epoxidation; (2) transformation of the epoxy alcohol to γ-hydroxyenal derivative; and (3) the Wittig reaction to furnish the Z -olefin.

Stereoselective Synthesis of Maresin-Like Lipid Mediators