In:
Synlett, Georg Thieme Verlag KG, Vol. 30, No. 03 ( 2019-02), p. 343-347
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.
Type of Medium:
Online Resource
ISSN:
0936-5214
,
1437-2096
DOI:
10.1055/s-0037-1612011
Language:
German
Publisher:
Georg Thieme Verlag KG
Publication Date:
2019
detail.hit.zdb_id:
2042012-2
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