Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC

被引：39

作者：

Jung, ME

Berliner, JA

Angst, D

Yue, DW

Koroniak, L

Watson, AD

Li, RS

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[2] Univ Calif Los Angeles, Dept Med Cardiol, Los Angeles, CA 90095 USA

[3] Univ Calif Los Angeles, Dept Pathol, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 18期

关键词：

D O I：

10.1021/ol051415y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of the naturally occurring hydroxy ketone PEIPC 1, a compound that plays a role in endothelial activation in atherosclerosis, has been completed via a triply convergent preparation of a protected El derivative 13 from 3,5-diacetoxycyclopentene 7, pentane-1,5-diol, and vinyllithium, using Sharpless epoxidation and enzymatic resolution as key steps. Final coupling with lyso-PC 16 and silyl group deprotection gave PECK 2 and PEIPC 1, which showed the same activity as natural PECPC and PEIPC.

引用

收藏

页码：3933 / 3935

页数：3

相关论文

共 14 条

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

Acharya, HP ;

Kobayashi, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) :3481-3484

[2] A role for oxidized phospholipids in artherosclerosis [J].

Berliner, JA ;

Watson, AD .

NEW ENGLAND JOURNAL OF MEDICINE, 2005, 353 (01) :9-11

[3] Oxidized phospholipid-induced endothelial cell/monocyte interaction is mediated by a cAMP-dependent R-Ras/PI3-kinase pathway [J].

Cole, AL ;

Subbanagounder, G ;

Mukhopadhyay, S ;

Berliner, JA ;

Vora, DK .

ARTERIOSCLEROSIS THROMBOSIS AND VASCULAR BIOLOGY, 2003, 23 (08) :1384-1390

[4] 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

[5]

JUNG ME, 2003, J CHEM SOC CHEM COMM, P167

[6] UNDERSTANDING ALLYLIC ORGANOCUPRATES - SIGMA-BOUND OR PI-BOUND REAGENTS [J].

LIPSHUTZ, BH ;

ELLSWORTH, EL ;

DIMOCK, SH ;

SMITH, RAJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (21) :4977-4979

[7] LIGAND-EXCHANGE BETWEEN CYANOCUPRATES AND ALLYLIC STANNANES - A NOVEL, DIRECT ROUTE TO ALLYLIC CUPRATES POSSESSING REMARKABLE REACTIVITY AND STABILITY [J].

LIPSHUTZ, BH ;

CROW, R ;

DIMOCK, SH ;

ELLSWORTH, EL ;

SMITH, RAJ ;

BEHLING, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4063-4064

[8] PROSTAGLANDIN SYNTHESES BY 3-COMPONENT COUPLING [J].

NOYORI, R ;

SUZUKI, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (11) :847-876

[9]

NOYORI R, 1990, CHEMTRACTS ORG CHEM, V3, P173

[10] A SHORT ENANTIOSPECIFIC SYNTHESIS OF THE CEROPLASTIN NUCLEUS [J].

SNIDER, BB ;

YANG, K .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3615-3626