A concise and efficient total synthetic route of active stilbene dimer (±)- ε-viniferin

Qibin Zhu; Binhao Teng; Ying Chen; Fubao Su; Yanqiu Li; Qingyun Yang; Chunsuo Yao

doi:10.1039/d2ra01385a

A concise and efficient total synthetic route of active stilbene dimer (±)- ε-viniferin

RSC Adv. 2022 Apr 8;12(18):11100-11103. doi: 10.1039/d2ra01385a. eCollection 2022 Apr 7.

Authors

Qibin Zhu¹, Binhao Teng¹, Ying Chen¹, Fubao Su¹, Yanqiu Li¹, Qingyun Yang¹, Chunsuo Yao¹

Affiliation

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College Beijing 100050 P. R. China yaocs@imm.ac.cn.

Abstract

A concise and efficient procedure for the total synthesis of natural stilbene dimer (±)-ε-viniferin was accomplished with high overall yield. Demethylation of the key intermediate methyl 3-arylbenzofuran-4-carboxylate was achieved successfully through bromination followed by BBr₃-or BCl₃/TBAI-mediated ether cleavage reaction. Pd/C and bromobenzene-catalyzed MOM ether cleavage was successfully carried out to aquire (±)-ε-viniferin.