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

Matokah Abualnaja; Paul G. Waddell; William Clegg; Michael J. Hall

doi:10.1016/j.tet.2016.08.008

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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

Journal article

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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

Matokah Abualnaja, Paul G. Waddell, William Clegg and Michael J. Hall

Tetrahedron, Vol.72(38), pp.5798-5806

22/09/2016

DOI: https://doi.org/10.1016/j.tet.2016.08.008

Abstract

Chemistry

Chemistry, Organic

Physical Sciences

Science & Technology

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.

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Title: Synthesis of pentacyclic pyrrolo[3,4-a]carbazole-1,3(2H)-diones via an intermolecular Diels-Alder, intramolecular carbonyl-ene reaction strategy
Creators - without role: Matokah Abualnaja - University of Newcastle Australia
Paul G. Waddell - Newcastle University
William Clegg - Newcastle University
Michael J. Hall - Newcastle Univ, Sch Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
Publication Details: Tetrahedron, Vol.72(38), pp.5798-5806
Publisher: Elsevier
Number of pages: 9
Grant note: Umm al-Qura University EP/I033959/1 / Engineering and Physical Sciences Research Council; UK Research & Innovation (UKRI); Engineering & Physical Sciences Research Council (EPSRC) EP/I033959/1 / Newcastle University and EPSRC; UK Research & Innovation (UKRI); Engineering & Physical Sciences Research Council (EPSRC) EP/I033959/1 / EPSRC; UK Research & Innovation (UKRI); Engineering & Physical Sciences Research Council (EPSRC)
Identifiers: 9931894508331
Academic Unit: Umm Al Qura University
Language: English
Resource Type: Journal article