Total synthesis of a potent proinflammatory 5-oxo-ETE and its 6,7-dihydro biotransformation product

被引：54

作者：

Khanapure, SP

Shi, XX

Powell, WS

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] McGill Univ, Meakins Christie Labs, Quebec City, PQ H2X 2P2, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 02期

关键词：

D O I：

10.1021/jo9716993

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of a potent inflammatory mediator 5-oxo-6(E),8(Z), 11(Z),14(Z)-eicosatetraenoic acid (5-oxo-ETE) 2 and its biotransformation product 6,7-dihydro-5-oxo-ETE 5 is reported. A convergent synthesis for the unstable title compounds is accomplished via two synthons, dithiolane aldehyde 13 and bisdienyl phosphonium bromide 19. The synthetic 5-oxo-ETE 2 and its 8,9-trans isomer 3 were used to unequivocally confirm the structure of the biologically derived mediators. In addition, using synthetic 6,7-dihydro-5-oxo-ETE 5 we have been able to identify in neutrophils the formation of 6,7-dihydro-5-oxo-ETE 5.

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页码：337 / 342

页数：6

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