Synthesis of methyl (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-7,9,11,13-hexadecatetraenoate, an analogue of 15R-lipoxin A4

被引:20
作者
Phillips, ED [1 ]
Chang, HF [1 ]
Holmquist, CR [1 ]
McCauley, JP [1 ]
机构
[1] AstraZeneca R&D Wilmington, Dept Chem, Wilmington, DE 19850 USA
关键词
D O I
10.1016/S0960-894X(03)00667-X
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
We describe a method for the synthesis of methyl (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-7,9,11,13-hexadecatetraenoate, a compound that has been described as a metabolically stable analogue of 15R-lipoxin A(4). (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3223 / 3226
页数:4
相关论文
共 29 条
[1]  
AKRITOPOULOUZAN.I, 1994, THESIS U SO CALIFORN
[2]  
Arbusow B.A., 1964, PURE APPL CHEM, V9, P307, DOI DOI 10.1351/PAC196409020307
[3]   STEREOSPECIFIC SYNTHESES AND SPECTROSCOPIC PROPERTIES OF ISOMERIC 2,4,6,8-UNDECATETRAENES - NEW HYDROCARBONS FROM THE MARINE BROWN ALGA-GIFFORDIA-MITCHELLAE .4. [J].
BOLAND, W ;
SIELER, C ;
FEIGEL, M .
HELVETICA CHIMICA ACTA, 1987, 70 (04) :1025-1040
[4]   Local and systemic delivery of a stable aspirin-triggered lipoxin prevents neutrophil recruitment in vivo [J].
Clish, CB ;
O'Brien, JA ;
Gronert, K ;
Stahl, GL ;
Petasis, NA ;
Serhan, CN .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (14) :8247-8252
[5]   PREPARATION OF TRANS-1,2-BIS(TRI-NORMAL-BUTYLSTANNYL)ETHYLENE [J].
COREY, EJ ;
WOLLENBERG, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (25) :3788-3789
[6]   Novel lipid mediator regulators of endothelial cell proliferation and migration:: Aspirin-triggered-15R-lipoxin A4 and lipoxin A4 [J].
Fierro, IM ;
Kutok, JL ;
Serhan, CN .
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2002, 300 (02) :385-392
[7]  
GERVITZ AT, 2002, J IMMUNOL, V168, P5260
[8]  
Godson C, 2000, Curr Opin Investig Drugs, V1, P380
[9]   THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].
KATSUKI, T ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976
[10]   A HIGHLY EFFICIENT SYNTHESIS OF PROSTAGLANDIN OMEGA-CHAIN PRECURSORS [J].
KITANO, Y ;
MATSUMOTO, T ;
OKAMOTO, S ;
SHIMAZAKI, T ;
KOBAYASHI, Y ;
SATO, F .
CHEMISTRY LETTERS, 1987, (08) :1523-1526