Issue 16, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
26 Apr 2018
Accepted
08 Jul 2018
First published
09 Jul 2018

New J. Chem., 2018,42, 13549-13557

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, 42, 13549 DOI: 10.1039/C8NJ02037J

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