Total synthesis of 2-(5,6-epoxyisoprostane A2)phosphorylcholine and elucidation of the relative configuration of the isoprostane moiety

被引：33

作者：

Acharya, HP ^{[1
]}

Kobayashi, Y ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 22期

关键词：

aldol reaction; isoprostanes; phospholipids; phosphorcholine; total synthesis;

D O I：

10.1002/anie.200500534

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) The two possible diastereomers of 5,6-epoxyisoprostane A2 were synthesized efficiently through aldol condensations of a substituted cyclopentenone and the corresponding epoxyaldehydes (see picture). The relative configurations of the products were assigned by comparing their 1H NMR spectra with literature data. Condensation of the epoxyisoprostane A2 with lysophosphorylcholine (lyso-PC) then furnished the title lipid. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3481 / 3484

页数：4

共 42 条

[1] Total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and related compounds [J].

Acharya, HP ;

Kobayashi, Y .

TETRAHEDRON LETTERS, 2004, 45 (06) :1199-1202

[2] Lipid oxidation products and atherosclerosis [J].

Berliner, J .

VASCULAR PHARMACOLOGY, 2002, 38 (04) :187-191

[3] Evidence for a role of phospholipid oxidation products in atherogenesis [J].

Berliner, JA ;

Subbanagounder, G ;

Leitinger, N ;

Watson, AD ;

Vora, D .

TRENDS IN CARDIOVASCULAR MEDICINE, 2001, 11 (3-4) :142-147

[4] Decreased lesion formation in CCR2-/- mice reveals a role for chemokines in the initiation of atherosclerosis [J].

Boring, L ;

Gosling, J ;

Cleary, M ;

Charo, IF .

NATURE, 1998, 394 (6696) :894-897

[5] SYNTHESIS AND PLATELET-AGGREGATION INHIBITING ACTIVITY OF PROSTAGLANDIN-D ANALOGS [J].

BUNDY, GL ;

MORTON, DR ;

PETERSON, DC ;

NISHIZAWA, EE ;

MILLER, WL .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (06) :790-799

[6] AN EFFICIENT METHOD FOR THE PARTIAL SYNTHESIS OF MIXED-CHAIN PHOSPHATIDYLETHANOLAMINES [J].

DELFINO, JM ;

SCHREIBER, SL ;

RICHARDS, FM .

TETRAHEDRON LETTERS, 1987, 28 (21) :2327-2330

[7] Total syntheses of iso-, neuro- and phytoprostanes: new insight in lipid chemistry [J].

Durand, T ;

Guy, A ;

Henry, O ;

Roland, A ;

Bernad, S ;

El Fangour, S ;

Vidal, JP ;

Rossi, JC .

CHEMISTRY AND PHYSICS OF LIPIDS, 2004, 128 (1-2) :15-33

[8] Synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] and its diastereoisomers [J].

Gaffney, PRJ ;

Reese, CB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (02) :192-205

[9] Oxidatively truncated docosahexaenoate phospholipids: Total synthesis, generation, and peptide adduction chemistry [J].

Gu, XR ;

Sun, MJ ;

Gugiu, B ;

Hazen, S ;

Crabb, JW ;

Salomon, RG .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :3749-3761

[10] Application of allylic substitutions in natural products synthesis [J].

Helmchen, G ;

Ernst, M ;

Paradies, G .

PURE AND APPLIED CHEMISTRY, 2004, 76 (03) :495-506

← 1 2 3 4 5 →