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

Authors :
You-Wei Hui
Xian-Fen Wang
Chun-Suo Yao
Yulong Kang
Zheng Wensheng
Jian-Qiao Zhang
Jin Wen
Jing-Shan Xie
Ji-Fa Zhang
Source :
Molecules, Volume 20, Issue 12, Pages 22662-22673, Molecules, Vol 20, Iss 12, Pp 22662-22673 (2015), Molecules; Volume 20; Issue 12; Pages: 22662-22673
Publication Year :
2015
Publisher :
Multidisciplinary Digital Publishing Institute, 2015.

Abstract

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.

Details

Language :
English
ISSN :
14203049
Database :
OpenAIRE
Journal :
Molecules
Accession number :
edsair.doi.dedup.....e79b4ed0c4b9284ab87fdb80382feeec
Full Text :
https://doi.org/10.3390/molecules201219872