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Stereoselective Synthesis of Maresin-like Lipid Mediators.

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 ?-hydroxyenal derivative; and (3) the Wittig reaction to furnish the Z-olefin.

SUBMITTER: Hong S 

PROVIDER: S-EPMC6510270 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of Maresin-like Lipid Mediators.

Hong Song S   Lu Yan Y   Morita Masao M   Saito Shun S   Kobayashi Yuichi Y   Jun Bokkyoo B   Bazan Nicolas G NG   Xu Xiaoming X   Wang Yapin Y  

Synlett : accounts and rapid communications in synthetic organic chemistry 20190114 3

Maresin-L1 (14<i>S</i>,22-dihydroxy-docosa-4<i>Z</i>,7<i>Z</i>,10<i>Z</i>,12<i>E</i>,16<i>Z</i>,19<i>Z</i>-hexaenoic acid) and maresin-L2 (14<i>R</i>,22-dihydroxy-docosa-4<i>Z</i>,7<i>Z</i>,10<i>Z</i>,12<i>E</i>,16<i>Z</i>,19<i>Z</i>-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 r  ...[more]

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