Synthesis of pentacyclic pyrrolo[3,4-a]carbazole-1,3(2H)-diones via an intermolecular Diels-Alder, intramolecular carbonyl-ene reaction strategy

被引：14

作者：

Abualnaja, Matokah ^{[1
]}

Waddell, Paul G. ^{[1
]}

Clegg, William ^{[1
]}

Hall, Michael J. ^{[1
]}

机构：

[1] Newcastle Univ, Sch Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

TETRAHEDRON | 2016年 / 72卷 / 38期

基金：

英国工程与自然科学研究理事会;

关键词：

Heterocycle synthesis; Carbazole; Diels-Alder cycloaddition; Ene reaction; ACTIVE CARBAZOLE ALKALOIDS; ASYMMETRIC-SYNTHESIS; FUNCTIONALIZED TETRAHYDROCARBAZOLES; ENANTIOSELECTIVE SYNTHESIS; BRONSTED ACID; DIASTEREOSELECTIVE SYNTHESIS; CASCADE REACTIONS; NATURAL-PRODUCTS; METAL-FREE; 3-VINYLINDOLES;

D O I：

10.1016/j.tet.2016.08.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pentacyclic pyrrolo[3,4-a]carbazole-1,3(2H)-diones are accessed via two key synthetic steps, an intermolecular Diels-Alder (D-A) reaction between an N-protected 3-vinyl-1H-indole and N-methyl-maleimide, and a Lewis acid-catalysed intramolecular carbonyl-ene cyclisation reaction. Cyclopentyl-or cyclohexyl-containing scaffolds can be formed through variation in the length of the alkyl tether, whilst the observed stereospecificity of carbonyl-ene cyclisation supports a concerted mechanism. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：5798 / 5806

页数：9

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