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Issue 32, 2014
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Palladium mediated intramolecular multiple C–X/C–H cross coupling and C–H activation: synthesis of carbazole alkaloids calothrixin B and murrayaquinone A

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Abstract

Straightforward palladium mediated syntheses of calothrixin B and murrayaquinone A are described. Regioselective palladium mediated intramolecular multiple C–X/C–H cross coupling reaction on N-(4-((2-bromophenyl)amino)-2,5-dimethoxybenzyl)-N-(2-iodophenyl)acetamide followed by CAN oxidation afforded calothrixin B in excellent yield in two steps. A linear synthesis has also been developed for calothrixin B. Utilizing C–H functionalization as well as palladium mediated intramolecular C–X/C–H cross coupling reaction, murrayaquinone A synthesis was achieved. Overall, these synthetic methodologies provide an expedient entry to these biologically active alkaloids in a short reaction sequence.

Graphical abstract: Palladium mediated intramolecular multiple C–X/C–H cross coupling and C–H activation: synthesis of carbazole alkaloids calothrixin B and murrayaquinone A

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Supplementary files

Article information


Submitted
05 Mar 2014
Accepted
09 Apr 2014
First published
09 Apr 2014

Org. Biomol. Chem., 2014,12, 6105-6113
Article type
Paper
Author version available

Palladium mediated intramolecular multiple C–X/C–H cross coupling and C–H activation: synthesis of carbazole alkaloids calothrixin B and murrayaquinone A

S. A. Kaliyaperumal, S. Banerjee and S. K. U. K., Org. Biomol. Chem., 2014, 12, 6105
DOI: 10.1039/C4OB00493K

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