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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 (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 r ...[more]

PMID: 31086432

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