Stereoselective Synthesis of Maresin-like Lipid Mediators
Song Hong1,2, Yan Lu1, Masao Morita3
1Neuroscience Center of Excellence, Louisiana State University Health Sciences Center, New Orleans, LA 70112, U.S.A.
Abstract:
Maresin-L1 (14S,22-dihydroxy-docosa-4Z,7Z,10Z,12E,16Z,19Z-hexaenoic acid) and maresin-L2 (14R,22-dihydroxy-docosa-4Z,7Z,10Z,12E,16Z,19Z-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.
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