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
收藏
页码：3413 / 3428
页数：16
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