Total synthesis of aspirin-triggered 15-epi-lipoxin A4

被引：26

作者：

Rodríguez, AR ^{[1
]}

Spur, BW ^{[1
]}

机构：

[1] Univ Med & Dent New Jersey, Dept Cell Biol, SOM, Stratford, NJ 08084 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 35期

关键词：

palladium catalyst; eicosanoids; Katsuki Sharpless reactions; reduction;

D O I：

10.1016/S0040-4039(01)01187-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of aspirin-triggered 15-epi-LXA(4) has been achieved using a chiral pool strategy for the C1-C12 fragment starting from 2-deoxy-D-ribose. Sharpless catalytic AE generated the C15 chiral center with > 98% ee. The stereospecific (Z)-reduction of the conjugated trienyne to the tetraene was achieved with Zn(Cu, Ag) in aq. CH3OH at aq. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6057 / 6060

页数：4

共 31 条

[1] ENANTIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF LIPOXIN-A - STEREOCHEMICAL ASSIGNMENT OF THE NATURAL LIPOXIN-A AND ITS POSSIBLE BIOSYNTHESIS [J].

ADAMS, J ;

FITZSIMMONS, BJ ;

GIRARD, Y ;

LEBLANC, Y ;

EVANS, JF ;

ROKACH, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (02) :464-469

[2] A versatile route to conjugated hydroxy (E,Z,E,E)-tetraenoic acids: highly chemo- and stereoselective synthesis of lipoxin B-4 [J].

Alami, M ;

Crousse, B ;

Linstrumelle, G ;

Mambu, L ;

Larcheveque, M .

TETRAHEDRON-ASYMMETRY, 1997, 8 (17) :2949-2958

[3]

BOHLMANN F, 1982, LIEBIGS ANN CHEM, P1216

[4] 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

[5] An excellent nickel boride catalyst for the cis-selective semihydrogenation of acetylenes [J].

Choi, JS ;

Yoon, NM .

TETRAHEDRON LETTERS, 1996, 37 (07) :1057-1060

[6] THE EFFECTS OF LIPOXIN-A(4) ON AIRWAY RESPONSES IN ASTHMATIC SUBJECTS [J].

CHRISTIE, PE ;

SPUR, BW ;

LEE, TH .

AMERICAN REVIEW OF RESPIRATORY DISEASE, 1992, 145 (06) :1281-1284

[7] A STEREOCONTROLLED AND EFFECTIVE SYNTHESIS OF LEUKOTRIENE-B-(1) [J].

COREY, EJ ;

MARFAT, A ;

MUNROE, J ;

KIM, KS ;

HOPKINS, PB ;

BRION, F .

TETRAHEDRON LETTERS, 1981, 22 (12) :1077-1080

[8]

COREY EJ, 1989, TETRAHEDRON LETT, V32, P4181

[9] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[10] LIPOXIN-A4 INHIBITS PHOSPHOINOSITIDE HYDROLYSIS IN HUMAN NEUTROPHILS [J].

GRANDORDY, BM ;

LACROIX, H ;

MAVOUNGOU, E ;

KRILIS, S ;

CREA, AEG ;

SPUR, BW ;

LEE, TH .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 167 (03) :1022-1029

← 1 2 3 4 →