Stereocontrolled Access to Isoprostanes via a Bicyclo[3.3.0]octene Framework

被引：79

作者：

Oger, Camille ^{[1
]}

Brinkmann, Yasmin ^{[1
]}

Bouazzaoui, Samira ^{[1
]}

Durand, Thierry ^{[1
]}

Galano, Jean-Marie ^{[1
]}

机构：

[1] Univ Montpellier 2, Univ Montpellier 1, UMR CNRS 5247, IBMM,Inst Biomol Max Mousseron,Fac Pharm, F-34093 Montpellier 05, France

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 21期

关键词：

D O I：

10.1021/ol802104z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a simple and highly stereocontrolled strategy toward the total synthesis of isoprostanes based on a bicyclic alpha,beta-epoxy ketone intermediate 6. Bicyclo[3.3.0]octene scaffold permitted stereodirection of reagents allowing stereoselective epoxidation, diastereoselective ketone reduction, and regioselective epoxide opening otherwise not accessible with a simple cyclopentene framework.

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页码：5087 / 5090

页数：4

相关论文

共 34 条

[1] On the use of succinic anhydride as acylating agent for practical resolution of aryl-alkyl alcohols through lipase-catalyzed acylation [J].

Bouzemi, N ;

Debbeche, H ;

Aribi-Zouioueche, L ;

Fiaud, JC .

TETRAHEDRON LETTERS, 2004, 45 (03) :627-630

[2] PREFERENTIAL FORMATION OF 8-EPI-PROSTAGLANDIN-F2-ALPHA VIA THE CORRESPONDING ENDOPEROXIDE BY A BIOMIMETIC CYCLIZATION [J].

COREY, EJ ;

SHIH, C ;

SHIH, NY ;

SHIMOJI, K .

TETRAHEDRON LETTERS, 1984, 25 (44) :5013-5016

[3] A METHOD FOR THE SELECTIVE OXIDATION OF 1,4-DIOLS TO LACTOLS [J].

COREY, EJ ;

PALANI, A .

TETRAHEDRON LETTERS, 1995, 36 (20) :3485-3488

[4] Cardiovascular pharmacology and physiology of the isoprostanes [J].

Cracowski, Jean-Luc ;

Durand, Thierry .

FUNDAMENTAL & CLINICAL PHARMACOLOGY, 2006, 20 (05) :417-427

[5] BASE-PROMOTED REACTIONS OF EPOXIDES .2. 3,4- AND 5,6-EPOXYCYCLOOCTENE [J].

CRANDALL, JK ;

CHANG, LH .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (03) :532-&

[6]

Durand T, 2001, EUR J ORG CHEM, V2001, P809

[7] Synthesis of (-)-xialenon A by enantioselective α-deprotonation-rearrangement of a meso-epoxide [J].

Hodgson, DM ;

Galano, JM ;

Christlieb, M .

TETRAHEDRON, 2003, 59 (49) :9719-9728

[8] TOTAL SYNTHESIS OF 8-EPI-PGF(2-ALPHA) - A NOVEL STRATEGY FOR THE SYNTHESIS OF ISOPROSTANES [J].

HWANG, SW ;

ADIYAMAN, M ;

KHANAPURE, S ;

SCHIO, L ;

ROKACH, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10829-10830

[9]

Iimori T, 1997, CHEM PHARM BULL, V45, P207

[10] Analysis of oxidative stress and wound-inducible dinor isoprostanes F1 (phytoprostanes F1) in plants [J].

Imbusch, R ;

Mueller, MJ .

PLANT PHYSIOLOGY, 2000, 124 (03) :1293-1303

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