Total synthesis of 20-hydroxyhepoxilins A(3), new metabolites of the hepoxilin family of eicosanoids

Authors
Demin, PM Kochev, DM Manukina, TA Pace-Asciak, CR Pivnitsky, KK
Citation
Pm. Demin et al., Total synthesis of 20-hydroxyhepoxilins A(3), new metabolites of the hepoxilin family of eicosanoids, BIOORG KHIM, 24(10), 1998, pp. 778-786
Citations number
21
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANICHESKAYA KHIMIYA
ISSN journal
01323423 → ACNP
Volume
24
Issue
10
Year of publication
1998
Pages
778 - 786
Database
ISI
SICI code
0132-3423(199810)24:10<778:TSO2AN>2.0.ZU;2-Z
Abstract
An enantiodirected total synthesis of 20-hydroxyhepoxilins A(3), new eicosa noids of lipoxygenase metabolism of arachidonic acid, was performed. The sy nthetic samples were found to be identical to the major metabolite formed o n incubation of (8S)-hepoxilin A(3) with human neutrophils, which demonstra ted that it has the structure of (8S)-20-hydroxy-HxA(3).