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Molecules 2013, 18(9), 10334-10351; doi:10.3390/molecules180910334
Article

Palladium-Catalyzed Synthesis of Natural and Unnatural 2-, 5-, and 7-Oxygenated Carbazole Alkaloids from N-Arylcyclohexane Enaminones

, , ,  and *
Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, México D.F. 11340, Mexico
* Author to whom correspondence should be addressed.
Received: 5 July 2013 / Revised: 5 August 2013 / Accepted: 12 August 2013 / Published: 26 August 2013
(This article belongs to the Special Issue Palladium Catalysts)
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Abstract

A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment to afford the corresponding diarylamines. The latter were submitted to a Pd(II)-catalyzed cyclization and methylation processes to provide the desired carbazoles, including clausine V. Following an inverse strategy, a new and short total synthesis of glycoborine is also reported.
Keywords: 2-oxygenated carbazoles; enaminones; palladium(II) cyclization; clausine V; glycoborine 2-oxygenated carbazoles; enaminones; palladium(II) cyclization; clausine V; glycoborine
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Bautista, R.; Montoya, P.A.; Rebollar, A.; Burgueño, E.; Tamariz, J. Palladium-Catalyzed Synthesis of Natural and Unnatural 2-, 5-, and 7-Oxygenated Carbazole Alkaloids from N-Arylcyclohexane Enaminones. Molecules 2013, 18, 10334-10351.

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