Potassium Hexacyanoferrate (III)-Catalyzed Dimerization of Hydroxystilbene: Biomimetic Synthesis of Indane Stilbene Dimers

Molecules

Jing-Shan Xie¹  Jin Wen³  Xian-Fen Wang¹  Jian-Qiao Zhang¹  Ji-Fa Zhang¹  Yu-Long Kang¹  You-Wei Hui²  Wen-Sheng Zheng¹  Chun-Suo Yao¹ 

[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, China;School of Chemical Engineering, Northwest University, Xi’an 710069, China;Chinese Pharmaceutical Association, Beijing 100022, China;

关键词: potassium hexacyanoferrate (III);    indane stilbene dimer;    biomimetic synthesis;    hydroxystilbene;   

DOI  :  10.3390/molecules201219872

来源: mdpi

【 摘 要 】

Using potassium hexacyanoferrate (III)–sodium acetate as oxidant, the oxidative coupling reaction of isorhapontigenin and resveratrol in aqueous acetone resulted in the isolation of three new indane dimers 4, 6, and 7, together with six known stilbene dimers. Indane dimer 5 was obtained for the first time by direct transformation from isorhapontigenin. The structures and relative configurations of the dimers were elucidated using spectral analysis, and their possible formation mechanisms were discussed. The results indicate that this reaction could be used as a convenient method for the semi-synthesis of indane dimers because of the mild conditions and simple reaction products.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.