Open analogues of arcyriaflavin A.: Synthesis through Diels-Alder reaction between maleimides and 1-aryl-3-tert-butyldimethylsiloxy-1,3-butadienes

被引：32

作者：

Adeva, M ^{[1
]}

Sahagún, H ^{[1
]}

Caballero, E ^{[1
]}

de Clairac, RPL ^{[1
]}

Medarde, M ^{[1
]}

Tomé, F ^{[1
]}

机构：

[1] Univ Salamanca, Fac Farm, Lab Quim Organ & Farmaceut, E-37007 Salamanca, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 11期

关键词：

D O I：

10.1021/jo991815x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of a range of open analogues of arcyriaflavin A is described. The synthetic approach is based on the use of perhydroisoindole-1,3,5-triones as key intermediates, which were obtained via Diels-Alder methodology using 1-aryl-3-siloxy-1,3-butadienes as starting materials. Fischer indolization and aromatization processes afforded different methoxy-substituted arylpyrrolocarbazoles. The stereochemistry and conformation of the Diels-Alder products and the regiochemistry of the indolization reactions are supported by NMR and molecular modeling studies.

引用

页码：3387 / 3394

页数：8

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