Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids

被引：25

作者：

Banwell, Martin G. ^{[1
]}

Ma, Xinghua ^{[1
]}

Taylor, Rebecca M. ^{[1
]}

Willis, Anthony C. ^{[1
]}

机构：

[1] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 21期

关键词：

D O I：

10.1021/ol062020x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of N-methylindole (4) with 6,6-dibromobicyclo[3.1.0] hexane ( 5) in the presence of silver tetrafluoroborate affords conjugate 7 in 67% yield. This product can be readily elaborated to compounds 12b and 13b which embody the polycyclic frameworks associated with members of the hapalindole and fischerindole classes of alkaloids. The chiral-auxiliary-substituted 6,6-dibromobicyclo[3.1.0] hexanes 21 and 22 react with indole to give adducts likely to be useful in the enantioselective total synthesis of the title alkaloids.

引用

页码：4959 / 4961

页数：3