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

Lookup NU author(s): Matokah Abualnaja, Dr Paul Waddell, Emeritus Professor Bill CleggORCiD, Dr Michael HallORCiD

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Abstract

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.

Publication metadata

Author(s): Abualnaja M, Waddell PG, Clegg W, Hall MJ

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2016

Volume: 72

Issue: 38

Pages: 5798-5806

Print publication date: 22/09/2016

Online publication date: 03/08/2016

Acceptance date: 01/08/2016

Date deposited: 03/08/2016

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Pergamon Press

URL: http://dx.doi.org/10.1016/j.tet.2016.08.008

DOI: 10.1016/j.tet.2016.08.008

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