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Synthesis 2017; 49(18): 4357-4371
DOI: 10.1055/s-0036-1588467
DOI: 10.1055/s-0036-1588467
paper
Palladium-Catalyzed Synthesis of Diarylamines and 1- and 2-Oxygenated Carbazoles: Total Syntheses of Natural Alkaloids Clauraila A, Clausenal, Clausine P, and 7-Methoxy-O-methylmukonal
J.T. acknowledges SIP/IPN (Grants 20150917, 20161791 and 20170902) and CONACYT (Grant 178219) for financial support. R.I.H.-B. and D.Z.-Z. thank CONACYT for graduate scholarships awarded, and SIP/IPN (BEIFI) for scholarship complements. F.D. and J.T. are fellows of the EDI-IPN and COFAA-IPN programs.Further Information
Publication History
Received: 07 April 2017
Accepted after revision: 22 May 2017
Publication Date:
05 July 2017 (online)
Abstract
The scope and limitations of the strategy for the conversion of 2-anilinocyclohexenones and N-arylcyclohexane enaminones into the 1- and 2-oxygenated carbazole scaffolds, respectively, were evaluated. The one-pot palladium(0)-catalyzed aromatization/methylation process of the aforementioned substrates provided a diversity of the corresponding diarylamines. A subsequent palladium(II)-catalyzed cyclization of the latter delivered the desired 1- and 2-oxygenated carbazoles in good overall yields. Special attention was given to the synthesis of the uncommon 1,8-disubstituted carbazoles. This methodology was employed for the total synthesis of the naturally occurring clauraila A, clausenal, clausine P, and 7-methoxy-O-methylmukonal.
Key words
1- and 2-oxygenated carbazoles - diarylamines - palladium(II) coupling - clausenal - clausine PSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588467.
- Supporting Information
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