Diastereoselectivity in the transannular Diels-Alder reaction of a trans-trans-trans 14-membered macrocycle leading to steroids

被引:2
|
作者
Drouin, M [1 ]
Couturier, M [1 ]
Deslongchamps, P [1 ]
机构
[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,SYNTH ORGAN LAB,SHERBROOKE,PQ J1K 2R1,CANADA
关键词
D O I
10.1107/S0108270197009578
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel 14-membered macrocyclic ring with trans-trans-trans triene geometry, trimethyl (4E,10E,12E)-(1R*,14S*)-5-methyl-17-oxobicyclo[12.3.0]heptadeca-4,10,12-triene-1,8,8-tricarboxylate, C24H32O7, which usually undergoes a Diels-Alder cycloaddition upon formation, has been isolated. From four possible contractions, the transannular reaction produces three adducts from which trimethyl rac-(5 beta,9 beta,10 alpha)-17-oxoandrost-6-ene-3,3,18-tricarboxylate, C24H32O7, was isolated and crystallized.
引用
收藏
页码:1698 / 1701
页数:4
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