MACROCYCLIZATION THROUGH RADICAL-MEDIATED VINYLCYCLOPROPANE ALKENE CONDENSATION - FACILE ENTRY INTO THE BREFELDIN RING-SYSTEM

被引：36

作者：

FELDMAN, KS ^{[1
]}

BERVEN, HM ^{[1
]}

ROMANELLI, AL ^{[1
]}

PARVEZ, M ^{[1
]}

机构：

[1] UNIV CALGARY, DEPT CHEM, CALGARY T2N 1N4, ALBERTA, CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 24期

关键词：

D O I：

10.1021/jo00076a056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic products featuring an 11-membered ring fused to a core vinylcyclopentane unit are produced upon treatment of functionalized vinylcyclopropanes bearing an omega-alkene unit with a catalytic amount of phenylthio radical. This intramolecular extension of a radical-mediated vinylcyclopropane/alkene cyclocondensation proceeds with only modest diastereoselectivity. The reaction products resemble members of the brefeldin family of naturally occurring antibiotics.

引用

页码：6851 / 6856

页数：6

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