Citation: Gangsheng Li, Xiang Yuan, Fu Liu, Zhihua Liu, Xujie Wang, Yuanyuan Liu, Yanmin Chen, Tingting Wang, Yanan Yang, Peicheng Zhang. Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade[J]. Chinese Chemical Letters, ;2025, 36(2): 109880. doi: 10.1016/j.cclet.2024.109880 shu

Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade

Gangsheng Li ^a ,
Xiang Yuan ^a ,
Fu Liu ^a ,
Zhihua Liu ^b ,
Xujie Wang ^a ,
Yuanyuan Liu ^b ,
Yanmin Chen ^b ,
Tingting Wang ^b ,
Yanan Yang ^{a, *,} ,
Peicheng Zhang ^{a, *,}

a.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
Beijing Wehand-Bio Pharmaceutical Co., Ltd., Beijing 100500, China

yyn@imm.ac.cn

pczhang@imm.ac.cn

Received Date: 1 February 2024
Revised Date: 1 April 2024
Accepted Date: 9 April 2024
Available Online: 10 April 2024

Figures(4)

The first synthesis of flavanostilbenes with a 2-cyclohepten-1-one core was carried out by applying an effective strategy in three steps from abundant polymerized flavanol resources. A key regio- and stereoselective Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade was explored and applied without the use of protecting groups, and water as an environmentally friendly solvent contributed to the cascade. The intramolecular [5 + 2] cycloaddition mechanism, involving oxidation and dearomatization of the flavanol unit as a diene, was proposed and supported by the synthesis of the intermediate. The regioselectivity of the cyclization was found to be dependent on the substitution effects of the stilbene units by the exploration of substrate scope.
- [5 + 2] Cycloaddition,
- Biomimetic synthesis,
- Copper,
- Natural products,
- Substrate
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