| Literature DB >> 31086432 |
Song Hong1,2, Yan Lu1, Masao Morita3, Shun Saito3, Yuichi Kobayashi3, Bokkyoo Jun1, Nicolas G Bazan1,2, Xiaoming Xu4, Yapin Wang4.
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.Entities:
Keywords: chiral LC-UV-MS/MS; diHDHA; lipid mediators; maresin-like; stereoselective organic synthesis
Year: 2019 PMID： 31086432 PMCID： PMC6510270 DOI： 10.1055/s-0037-1612011
Source DB: PubMed Journal: Synlett ISSN： 0936-5214 Impact factor: 2.454