FREE-RADICAL MACROCYCLIZATION VIA PROPIOLATE ESTERS

被引：30

作者：

BALDWIN, JE

ADLINGTON, RM

RAMCHARITAR, SH

机构：

[1] The Dyson Perrins Laboratory, University of Oxford, Oxford, OX1 3QY, South Parks Road

来源：

TETRAHEDRON | 1992年 / 48卷 / 16期

关键词：

RADICAL; MACROCYCLIZATION; PROPIOLATE ESTER; MACROCYCLIC UNSATURATED LACTONE; HIGH DILUTION;

D O I：

10.1016/0040-4020(92)85015-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular free-radical addition to propiolate esters has provided a new and a stereoselective route to 14-16 membered trans- alpha,beta-unsaturated macrocyclic lactones from their corresponding omega-iodoalkyl-propiolate esters under triphenyltin hydride/AIBN mediated conditions. Attempts to synthesise analogous 10-13 membered lactones proved unsuccessful, resulting in acyclic products derived from direct reduction at the radical centre.

引用

页码：3413 / 3428

页数：16