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
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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