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Molecules 2017, 22(5), 742; doi:10.3390/molecules22050742

AlCl3·6H2O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol

1
School of Pharmaceutical Sciences, Fujian Provincial Key Laboratory of Innovative Drug Target Research, Xiamen University, Xiamen 361102, China
2
Sanford Burnham Prebys Medical Discovery Institute, 10901 N. Torrey Pines Road, La Jolla, CA 92037, USA
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editors: Qing-Wen Zhang and Chuang-Chuang Li
Received: 8 March 2017 / Revised: 26 April 2017 / Accepted: 27 April 2017 / Published: 16 May 2017
(This article belongs to the Special Issue Synthesis and Modification of Natural Product)
View Full-Text   |   Download PDF [2703 KB, uploaded 16 May 2017]   |  

Abstract

A classical Friedel-Crafts alkylation of different indoles catalyzed by AlCl3·6H2O has been developed for a well-known important natural product, celastrol, resulting in a series of derivatives for further biological evaluation. The catalyst loading was reduced to 5 mol %, the reaction proceeds at ambient temperature and reaction time is only 3 h. The product yields range from 20% to 99%. A reaction mechanism is also proposed, based on our experiment results. View Full-Text
Keywords: celastrol; indole; Friedel-Crafts alkylation; AlCl3·6H2O celastrol; indole; Friedel-Crafts alkylation; AlCl3·6H2O
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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. (CC BY 4.0).

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Zhu, Y.; Chen, Z.; Huang, Z.; Yan, S.; Li, Z.; Zhou, H.; Zhang, X.; Su, Y.; Zeng, Z. AlCl3·6H2O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol. Molecules 2017, 22, 742.

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