A short catalytic enantioselective synthesis of the proinflammatory eicosanoid 12(R)-hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic acid (12(R)-HETE)

被引：17

作者：

Han, XJ ^{[1
]}

Corey, EJ ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 16期

关键词：

D O I：

10.1021/ol0062392

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new and effective pathway is described for the synthesis of 12(R)-HETE and the 12(S)-enantiomer from the common intermediates 4 and 8.

引用

页码：2543 / 2544

页数：2

共 41 条

[1] Resistance to type 1 diabetes induction in 12-lipoxygenase knockout mice [J].

Bleich, D ;

Chen, SY ;

Zipser, B ;

Sun, DX ;

Funk, CD ;

Nadler, JL .

JOURNAL OF CLINICAL INVESTIGATION, 1999, 103 (10) :1431-1436

[2] A 12R-lipoxygenase in human skin: Mechanistic evidence, molecular cloning, and expression [J].

Boeglin, WE ;

Kim, RB ;

Brash, AR .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (12) :6744-6749

[3] Induction of 12-lipoxygenase expression by transforming growth factor-α in human epidermoid carcinoma A431 cells [J].

Chen, LC ;

Chen, BK ;

Liu, YW ;

Chang, WC .

FEBS LETTERS, 1999, 455 (1-2) :105-110

[4] TOTAL SYNTHESIS OF (S)-12-HYDROXY-5,8,14-CIS-10-TRANS-EICOSATETRAENOIC ACID (SAMUELSSONS HETE) [J].

COREY, EJ ;

NIWA, H ;

KNOLLE, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (06) :1942-1943

[5] A SHORT 3-COMPONENT TOTAL SYNTHESIS OF 12-HYDROXYEICOSA-5,8,14(Z),10(E)-TETRAENOIC ACID (12-HETE) VIA THE CORRESPONDING KETONE [J].

COREY, EJ ;

KYLER, K ;

RAJU, N .

TETRAHEDRON LETTERS, 1984, 25 (45) :5115-5118

[6] CONTROLLED CHEMICAL SYNTHESIS OF THE ENZYMATICALLY PRODUCED EICOSANOIDS 11-HETE, 12-HETE, AND 15-HETE FROM ARACHIDONIC-ACID AND CONVERSION INTO THE CORRESPONDING HYDROPEROXIDES (HPETE) [J].

COREY, EJ ;

MARFAT, A ;

FALCK, JR ;

ALBRIGHT, JO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (04) :1433-1435

[7] 12(R)-HYDROXY-5,8,10,14-EICOSATETRAENOIC ACID IS A CHEMOATTRACTANT FOR HUMAN POLYMORPHONUCLEAR LEUKOCYTES INVITRO [J].

CUNNINGHAM, FM ;

WOOLLARD, PM .

PROSTAGLANDINS, 1987, 34 (01) :71-78

[8] Disruption of the 12/15-lipoxygenase gene diminishes atherosclerosis in apo E-deficient mice [J].

Cyrus, T ;

Witztum, JL ;

Rader, DJ ;

Tangirala, R ;

Fazio, S ;

Linton, MF ;

Funk, CD .

JOURNAL OF CLINICAL INVESTIGATION, 1999, 103 (11) :1597-1604

[9] Lipoxygenase inhibitors abolish proliferation of human pancreatic cancer cells [J].

Ding, XZ ;

Iversen, P ;

Cluck, MW ;

Knezetic, JA ;

Adrian, TE .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1999, 261 (01) :218-223

[10] MOLECULAR-CLONING, PRIMARY STRUCTURE, AND EXPRESSION OF THE HUMAN PLATELET ERYTHROLEUKEMIA CELL 12-LIPOXYGENASE [J].

FUNK, CD ;

FURCI, L ;

FITZGERALD, GA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (15) :5638-5642

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