FORMATION OF TRANS RING-FUSED COMPOUNDS BY AN ALKYLATION-RADICAL CYCLIZATION SEQUENCE

被引:28
作者
CLIVE, DLJ
MANNING, HW
BOIVIN, TLB
POSTEMA, MHD
机构
[1] Department of Chemistry, University of Alberta, Edmonton, Alberta
关键词
D O I
10.1021/jo00076a057
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enolates derived from bicyclic lactones of type 1 (Scheme I) can be alkylated with 2-propynylic halides to give products 2, in which the unsaturated alkyl group is syn to the adjacent ring-fusion hydrogen. Reaction of 2 with sodium phenyl selenide and then with diazomethane produces esters 3, and these give trans ring-fused bicyclic compounds 4 when treated with triphenyltin hydride in the presence of a radical initiator. The bicyclic compounds afford ketones on double-bond cleavage, and the angular ester function can be converted into a methyl group. Similar processes occur if an aldehyde is used in the first step instead of a halide. The methodology is general.
引用
收藏
页码:6857 / 6873
页数:17
相关论文
共 120 条