SYNTHESIS AND TRANSANNULAR DIELS-ALDER REACTION OF A 13-MEMBERED MACROCYCLIC TRIENE HAVING A TETRASUBSTITUTED ENOL ETHER AS DIENOPHILE

被引：22
作者：
BERUBE, G
DESLONGCHAMPS, P
机构：
[1] Laboratoire de Synthèse Organique, Department de Chimie, Université de Sherbrooke, Sherbrooke (QC)
来源：
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1990年 / 68卷 / 03期
关键词：
Diels-Alder reaction; Macrocyclic triene; Macrocyclization; Organic synthesis; Transannular process; Tricyclic compounds;
D O I：
10.1139/v90-062
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The syntheses of the acyclic triene trans-trans-cis 27 and trans-trans-trans 31 are described. Macrocyclization and concomitant transannular Diels-Alder reaction were performed with the chloride derivative obtained from the trans-trans-cis triene alcohol 27 yielding a mixture of the tricyclic compounds trans-syn-trans 33 and cis-syn-cis 34. On the other hand, macrocyclization of the chloride derived from trans-trans-trans triene 31 was not successful.
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页码：404 / 411
页数：8
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