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Palladium and Organocatalysis: An Excellent Recipe for Asymmetric Synthesis
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 *
Received: 5 July 2013; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Bautista R, Montoya PA, 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(9):10334-10351.

Chicago/Turabian Style

Bautista, Rafael; Montoya, Pablo A.; Rebollar, Araceli; Burgueño, Eleuterio; Tamariz, Joaquín. 2013. "Palladium-Catalyzed Synthesis of Natural and Unnatural 2-, 5-, and 7-Oxygenated Carbazole Alkaloids from N-Arylcyclohexane Enaminones." Molecules 18, no. 9: 10334-10351.


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