STEREOCONTROLLED CONSTRUCTION OF A.B.C.[6.6.6] TRICYCLE VIA TRANSANNULAR DIELS-ALDER REACTION OF 14-MEMBERED TRIENE MACROCYCLE

被引：6

作者：

CANTIN, M ^{[1
]}

XU, YC ^{[1
]}

DESLONGCHAMPS, P ^{[1
]}

机构：

[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,SYNTHESE ORGAN LAB,SHERBROOKE J1K 2R1,QUEBEC,CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1990年 / 68卷 / 12期

关键词：

STEREOCONTROLLED SYNTHESIS; MACROCYCLE; TRICYCLIC COMPOUND; TRANSANNULAR DIELS-ALDER REACTION;

D O I：

10.1139/v90-329

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of the four acyclic trienes 11a, b and 20a, b is reported. The tandem macrocyclization and stereoselective transannular Diels-Alder reaction of acyclic trienes 11b (trans-trans-cis) and 20b (trans-trans-trans) were observed in the presence of Cs2CO3 at 85-degrees-C to give tricycles 30 (TST) and 32 (CAT) respectively. However, treatment of acyclic trienes 11a (cis-trans-cis) and 20a (cis-trans-trans) under the same conditions yielded the 14-membered macrocycles 21 and 23, which were stereoselectively transformed at 250-degrees-C into tricycles 22 (CST) and 24 (CAT) respectively in excellent yield.

引用

页码：2144 / 2152

页数：9