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- Hong, S, et al.
(author)
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Stereoselective Synthesis of Maresin-like Lipid Mediators
- 2019
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In: Synlett : accounts and rapid communications in synthetic organic chemistry. - : Georg Thieme Verlag KG. - 0936-5214. ; 30:3, s. 343-347
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Journal article (peer-reviewed)abstract
- 14S,22-Dihydroxy-docosa-4Z,7Z,10Z,12E,16Z,19Z-hexaenoic acid (maresin-L1) and 14R,22-dihydroxy-docosa-4Z,7Z,10Z, 12E,16Z,19Z-hexaenoic acid (maresin-L2) 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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