Synthesis of substituted bicyclo[2.2.2]octatrienes

被引：12

作者：

Wagaman, MW ^{[1
]}

Bellmann, E ^{[1
]}

Cucullu, M ^{[1
]}

Grubbs, RH ^{[1
]}

机构：

[1] CALTECH, Arnold & Mabel Beckman Labs Chem Synthesis, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 26期

关键词：

D O I：

10.1021/jo971039y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient route to bicyclo[2.2.2]octatriene, barrelene, and substituted versions of this molecule has been developed starting from the benzene equivalent cis-3,5-cyclohexadiene-1,2-diol. Following the Diels-Alder reaction of this molecule with an activated acetylene, conversion of the diol to the final olefin was accomplished through formation of a thiocarbonate intermediate and subsequent reaction with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine (DPD). The synthesis developed allows a variety of barrelenes to be prepared in as few as three steps from commercially available starting materials.

引用

页码：9076 / 9082

页数：7

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