A NEW ENANTIOSELECTIVE APPROACH TO THE BICYCLO[4.4.0]DECANE AND BICYCLO[4.3.0]NONANE SYSTEMS

被引：8

作者：

ASAOKA, M

NISHIMURA, K

TAKEI, H

机构：

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1990年 / 63卷 / 02期

关键词：

D O I：

10.1246/bcsj.63.407

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly diasteroselective routes to cis-fused bicyclo[4.4.0]decane-2,10-diones and bicyclo[4.3.0]nonane-2,9-diones from 5-trimethylsilyl-2-cyclohexen-1 -one (1a) and its 3-methyl derivative were established by utilizing an annulation with Ω-(alkoxycarbonyl)alkylzinc reagents. Bicyclo[4.4.0]decane-2,8-dione was obtained diastereoselectively by the double Michael reaction of 1a with dienol silyl ether. The diastereoselective Diels-Alder reaction of 1a with cyclopentadiene gave an endo adduct, which can be regarded as a new chiral cyclohexenone synthon, with a high optical purity.

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页码：407 / 411

页数：5

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