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A concise synthesis of cyclobrassinin and its analogues via a thiyl radical aromatic substitution

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Abstract

A simple and concise approach for the synthesis of cyclobrassinin has been developed through a thiyl radical-mediated intramolecular aromatic substitution, with benzoyl peroxide as an efficient initiator and oxidant. The current method can also be utilized in the synthesis of 6 and 7-membered ring cyclobrassinin analogues in moderate to good yields. The transformation involves a formal radical 6 and 7-endo-trig cyclization of the corresponding dithiocarbamate derivatives, which were generated from indole-3-methanamines and tryptophan.

Graphical abstract: A concise synthesis of cyclobrassinin and its analogues via a thiyl radical aromatic substitution

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Publication details

The article was received on 26 Apr 2018, accepted on 08 Jul 2018 and first published on 09 Jul 2018


Article type: Paper
DOI: 10.1039/C8NJ02037J
Citation: New J. Chem., 2018, Advance Article
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    A concise synthesis of cyclobrassinin and its analogues via a thiyl radical aromatic substitution

    X. Zhong, N. Chen and J. Xu, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ02037J

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