Conversion of delta-(sulfonyl)amino-alpha-epoxy ketones to bicyclic ketopyrroles via intramolecular conjugate-addition to azoene intermediates. Synthesis of the bicyclic ketopyrrole core of the 1-azafulvene roseophilin.

被引：31

作者：

Kim, SH ^{[1
]}

Fuchs, PL ^{[1
]}

机构：

[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 15期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(96)00390-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of delta-(sulfonyl)amino-alpha-epoxy ketones with dimethylhydrazine results in cyclization to pyrrolidine-fused beta-hydroxy dimethylhydrazones. elimination affords dihydropyrroles which can be converted to sulfonyl-protected ketopyrroles via oxidation with NIS; alternatively, treatment with DBU affords N-H bearing ketopyrroles. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：2545 / 2548

页数：4

共 21 条

[1] CYCLOALKAPYRROLONES VIA DECARBOXYLATIVE RING CLOSURE OF PYRROLE-3-ALKANOIC ACIDS AND DERIVATIVES [J].