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

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
2
School of Chemical Engineering, Northwest University, Xi’an 710069, China
3
Chinese Pharmaceutical Association, Beijing 100022, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Molecules 2015, 20(12), 22662-22673; https://doi.org/10.3390/molecules201219872
Received: 16 November 2015 / Revised: 7 December 2015 / Accepted: 9 December 2015 / Published: 18 December 2015
(This article belongs to the Section Bioorganic Chemistry)
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. View Full-Text
Keywords: potassium hexacyanoferrate (III); indane stilbene dimer; biomimetic synthesis; hydroxystilbene potassium hexacyanoferrate (III); indane stilbene dimer; biomimetic synthesis; hydroxystilbene
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MDPI and ACS Style

Xie, J.-S.; Wen, J.; Wang, X.-F.; Zhang, J.-Q.; Zhang, J.-F.; Kang, Y.-L.; Hui, Y.-W.; Zheng, W.-S.; Yao, C.-S. Potassium Hexacyanoferrate (III)-Catalyzed Dimerization of Hydroxystilbene: Biomimetic Synthesis of Indane Stilbene Dimers. Molecules 2015, 20, 22662-22673.

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