Radical aryl migration enables diversity-oriented synthesis of structurally diverse medium/macro- or bridged-rings

Lei Li, Zhong-Liang Li, Fu-Li Wang, Zhen Guo, Yong-Feng Cheng, Na Wang, Xiao-Wu Dong, Chao Fang, Jingjiang Liu, Chunhui Hou, Bin Tan and Xin-Yuan Liu ()
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Lei Li: South University of Science and Technology of China
Zhong-Liang Li: South University of Science and Technology of China
Fu-Li Wang: South University of Science and Technology of China
Zhen Guo: College of Materials Science & Engineering, Taiyuan University of Technology
Yong-Feng Cheng: South University of Science and Technology of China
Na Wang: College of Materials Science & Engineering, Taiyuan University of Technology
Xiao-Wu Dong: College of Pharmaceutical Sciences, Zhejiang University
Chao Fang: South University of Science and Technology of China
Jingjiang Liu: South University of Science and Technology of China
Chunhui Hou: South University of Science and Technology of China
Bin Tan: South University of Science and Technology of China
Xin-Yuan Liu: South University of Science and Technology of China

Nature Communications, 2016, vol. 7, issue 1, 1-11

Abstract: Abstract Medium-sized and medium-bridged rings are attractive structural motifs in natural products and therapeutic agents. Due to the unfavourable entropic and/or enthalpic factors with these ring systems, their efficient construction remains a formidable challenge. To address this problem, we herein disclose a radical-based approach for diversity-oriented synthesis of various benzannulated carbon- and heteroatom-containing 8–11(14)-membered ketone libraries. This strategy involves 1,4- or 1,5-aryl migration triggered by radical azidation, trifluoromethylation, phosphonylation, sulfonylation, or perfluoroalkylation of unactivated alkenes followed by intramolecular ring expansion. Demonstration of this method as a highly flexible tool for the construction of 37 synthetically challenging medium-sized and macrocyclic ring scaffolds including bridged rings with diverse functionalities and skeletons is highlighted. Some of these products showed potent inhibitory activity against the cancer cell or derivative of human embryonic kidney line in preliminary biological studies. The mechanism of this novel strategy is investigated by control experiments and DFT calculations.

Date: 2016
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DOI: 10.1038/ncomms13852

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