Total syntheses of iso-, neuro- and phytoprostanes: new insight in lipid chemistry

被引：19

作者：

Durand, T ^{[1
]}

Guy, A ^{[1
]}

Henry, O ^{[1
]}

Roland, A ^{[1
]}

Bernad, S ^{[1
]}

El Fangour, S ^{[1
]}

Vidal, JP ^{[1
]}

Rossi, JC ^{[1
]}

机构：

[1] Univ Montpellier I, Fac Pharm, CNRS, UMR 5074, F-34093 Montpellier 5, France

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 2004年 / 128卷 / 1-2期

关键词：

radical cyclization; total syntheses; metabolites; isoprostanes; neuroprostares; phytoprostanes; wittig; HWE;

D O I：

10.1016/j.chemphyslip.2003.10.008

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Isoprostanes (IsoPs) are a complex family of compounds produced, in vivo, from peroxidation of polyunsaturated fatty acids (AA. DHA, EPA, alpha-linolenic) via a free-radical-catalyzed mechanism. Carbocyclic annulations are extremely important reactions and the stereocontrolled intramolecular free-radical cyclization has emerged as a powerful tool for carbon-carbon bond formation in synthetic chemistry. The hex-5-enyl radical cyclization is the most well-known for the synthesis of cyclopentane rings. After a short review of the literature, concerning the total synthesis of isoprostanes and intermediates, we will present our own contributions on the preparation of chiral cyclopentane rings from glucose leading to new isoprostanes. This study allowed us to control the cyclization outcome to yield the all-syn and/or syn-anti-syn precursors which permit us to the total synthesis of a large set of iso-, neuro-, and phytoprostanes. (C) 2003 Elsevier Ireland Ltd. All rights reserved.

引用

页码：15 / 33

页数：19

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