A FREE-RADICAL ROUTE TO SYN LACTONES AND OTHER PROSTANOID INTERMEDIATES IN ISOPROSTAGLANDIN SYNTHESIS

被引：41

作者：

RONDOT, B ^{[1
]}

DURAND, T ^{[1
]}

GIRARD, JP ^{[1
]}

ROSSI, JC ^{[1
]}

SCHIO, L ^{[1
]}

KHANAPURE, SP ^{[1
]}

ROKACH, J ^{[1
]}

机构：

[1] FLORIDA INST TECHNOL,CLAUDE PEPPER INST AGING & THERAPEUT RES,MELBOURNE,FL 32901

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(00)61401-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hex-5-enyl radical cyclization methodology was applied to the formation of optical active prostanoid intermediates ($) under bar 7,($) under bar 8,($) under bar 9 with readily available diacetone-D-glucose as starting material. This result should lead to isoprostaglandins, a navel class of arachidonic acid metabolites obtained by a non-cyclooxygenase mechanism involving free radical-catalysed peroxidation of arachidonic acid.

引用

页码：8245 / 8248

页数：4

共 12 条

[1] TRIS(TRIMETHYLSILYL)SILANE AS A RADICAL-BASED REDUCING AGENT IN SYNTHESIS [J].

BALLESTRI, M ;

CHATGILIALOGLU, C ;

CLARK, KB ;

GRILLER, D ;

GIESE, B ;

KOPPING, B .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :678-683

[2] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[3] PREFERENTIAL CIS CYCLIZATION OF 6-HEPTEN-2-YL AND RELATED RADICALS - EXAMPLE OF ORBITAL SYMMETRY CONTROL [J].

BECKWITH, AL ;

BLAIR, I ;

PHILLIPO.G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (05) :1613-1614

[4] ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS [J].

CHATGILIALOGLU, C .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) :188-194

[5] PREFERENTIAL FORMATION OF 8-EPI-PROSTAGLANDIN-F2-ALPHA VIA THE CORRESPONDING ENDOPEROXIDE BY A BIOMIMETIC CYCLIZATION [J].

COREY, EJ ;

SHIH, C ;

SHIH, NY ;

SHIMOJI, K .

TETRAHEDRON LETTERS, 1984, 25 (44) :5013-5016

[6] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (06) :417-439

[7]

GRANGER R, 1967, CR ACAD SCI C CHIM, V264, P1717

[8] EFFICIENT FREE-RADICAL AND PALLADIUM-CATALYZED TANDEM ALKENE INSERTIONS - A NEW APPROACH TO BENZOPROSTACYCLINS [J].

LAROCK, RC ;

LEE, NH .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6253-6254

[9] A SERIES OF PROSTAGLANDIN-F2-LIKE COMPOUNDS ARE PRODUCED INVIVO IN HUMANS BY A NONCYCLOOXYGENASE, FREE RADICAL-CATALYZED MECHANISM [J].

MORROW, JD ;

HILL, KE ;

BURK, RF ;

NAMMOUR, TM ;

BADR, KF ;

ROBERTS, LJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (23) :9383-9387

[10] FROM CARBOHYDRATES TO OPTICALLY-ACTIVE CARBOCYCLES .1. STEREOCHEMICAL CONTROL IN SUGAR HEX-5-ENYL RADICAL CYCLIZATION [J].

RAJANBABU, TV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (02) :609-611

← 1 2 →