Electrochemical collective synthesis of labeled pyrroloindoline alkaloids with Freon-type methanes as functional C1 synthons

Utilization of Freon-type methanes as functional one-carbon synthons in the synthesis of various deuterated indoline alkaloids was demonstrated here. A series of halomethyl radicals were generated from electro-reductive C-X cleavage of Freon-type methanes and captured efficiently by acrylamides to p...

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Published in:Chemical communications (Cambridge, England) England), 2022-08, Vol.58 (66), p.923-9233
Main Authors: Chen, Chao, Liu, Ru-Xin, Xiong, Feng, Li, Zi-Hao, Kang, Jun-Chen, Ding, Tong-Mei, Zhang, Shu-Yu
Format: Article
Language:English
Subjects:
Alkaloids
Chemical synthesis
Deuteration
Deuterium
Fluorine
Freons
Functional groups
Physostigmine
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Summary:Utilization of Freon-type methanes as functional one-carbon synthons in the synthesis of various deuterated indoline alkaloids was demonstrated here. A series of halomethyl radicals were generated from electro-reductive C-X cleavage of Freon-type methanes and captured efficiently by acrylamides to provide various halogenated oxindoles via radical cyclization. This reaction features good functional group tolerance, and deuterium and fluorine atoms could be introduced facilely from Freon-type methanes. Further transformation of halogenated oxindoles enabled the synthesis of many (labeled) bioactive drug molecules and skeletons, such as deuterated (±)-physostigmine, deuterated (±)-esermethole and deuterated (±)-lansai B. Electrochemical radical cyclization of acrylamides with Freon-type methanes as functional C1 synthons provided various halogenated oxindoles, which could be transformed into various labeled pyrroloindoline alkaloids.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc03301a