Total synthesis of 8,12-iso-iPF3α-VI, an EPA-derived isoprostane:: Stereoselective introduction of the fifth asymmetric center

被引：34

作者：

Jacobo, SH

Chang, CT

Lee, GJ

Lawson, JA

Powell, WS

Pratico, D

FitzGerald, GA

Rokach, J

机构：

[1] Florida Inst Technol, Claude Pepper Inst, Melbourne, FL 32901 USA

[2] Florida Inst Technol, Dept Chem, Melbourne, FL 32901 USA

[3] Univ Penn, Ctr Expt Therapeut, Philadelphia, PA 19104 USA

[4] McGill Univ, Dept Med, Meakins Christie Labs, Montreal, PQ H2X 2P2, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 04期

关键词：

D O I：

10.1021/jo051916x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereochemistry of the hydroxy group. The first total synthesis of an eicosapentaenoic acid (EPA)-derived iP, 8,12-iso-iPF(3 alpha)-VI 10, was performed using this approach.

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页码：1370 / 1379

页数：10

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