Total Synthesis of Isoprostanes Derived from Adrenic Acid and EPA

被引：33
作者：
Oger, Camille [1 ,2 ]
Bultel-Ponce, Valerie [1 ,2 ]
Guy, Alexandre [1 ,2 ]
Durand, Thierry [1 ,2 ]
Galano, Jean-Marie [1 ,2 ]
机构：
[1] Univ Montpellier I, UMR 5247 CNRS, Inst Biomol Max Mousseron, Fac Pharm, F-34093 Montpellier 05, France
[2] Univ Montpellier 2, UMR 5247 CNRS, Inst Biomol Max Mousseron, Fac Pharm, F-34093 Montpellier 5, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 13期
关键词：
Biomarkers; Oxidation; Total synthesis; Natural products; AXIALLY DISSYMMETRIC MOLECULES; IN-VIVO; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE REDUCTION; SECONDARY ALCOHOLS; OXIDATIVE STRESS; PEROXIDATION; F-4-ISOPROSTANES; F-3-ISOPROSTANES; CHEMISTRY;
D O I：
10.1002/ejoc.201200070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantiomerically enriched F2-dihomo-isoprostanes and F3-isoprostanes have been synthesized. Such compounds are derived from the action of reactive oxygen species on the phospholipid-bound polyunsaturated fatty acids (PUFA), adrenic acid and eicosapentaenoic acid, respectively. Of special interest are the F2-dihomo-isoprostanes because they could represent potential biomarkers for myelin damage as its main PUFA constituent is adrenic acid. Our strategy, based on a pivotal enantiomerically enriched intermediate, has allowed access to F2-dihomo-IsoP and both C5 epimers of 5-F3t-IsoP for the first time.
引用
收藏
页码：2621 / 2634
页数：14
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