Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Key Laboratory for Thin Film and Microfabrication of Ministry of Education, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China.
Chem Commun (Camb). 2022 Aug 16;58(66):9230-9233. doi: 10.1039/d2cc03301a.
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 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.
在这里，我们展示了氟利昂型甲烷作为功能一碳合成子在各种氘代吲哚生物碱合成中的应用。一系列卤甲基自由基通过氟利昂型甲烷的电还原 C-X 裂解生成，并被丙烯酰胺有效地捕获，从而提供了各种卤代氧化吲哚自由基环化反应。该反应具有良好的官能团耐受性，并且可以从氟利昂型甲烷中容易地引入氘和氟原子。进一步转化卤代氧化吲哚可以合成许多（标记）生物活性药物分子和骨架，如氘代（±）-毒扁豆碱、氘代（±）-esermethole 和氘代（±）-lansai B。
