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. 2015 Dec 18;20(12):22662-73.
doi: 10.3390/molecules201219872.

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

Jing-Shan Xie  1   2 , Jin Wen  3 , Xian-Fen Wang  4 , Jian-Qiao Zhang  5 , Ji-Fa Zhang  6 , Yu-Long Kang  7 , You-Wei Hui  8 , Wen-Sheng Zheng  9 , Chun-Suo Yao  10
Affiliations

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

Jing-Shan Xie et al. Molecules. .

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.

Keywords: biomimetic synthesis; hydroxystilbene; indane stilbene dimer; potassium hexacyanoferrate (III).

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of compounds 3–11.
Figure 2
Figure 2
Analysis of isorhapontigenin oxidation products by K3Fe(CN)6/NaOAc (32% CH3CN/H2O, λ = 230 nm, 1 mL/min).
Figure 3
Figure 3
Analysis of resveratrol oxidation products by K3Fe(CN)6/NaOAc (52% MeOH/H2O, λ = 230 nm, 1 mL/min).
Figure 4
Figure 4
The significant HMBC (a) and NOESY (b) interactions of 4.
Figure 5
Figure 5
The key HMBC (a) and NOESY (b) correlations of 6.
Figure 6
Figure 6
The key HMBC (a) and NOESY (b) correlations of 7.
Scheme 1
Scheme 1
Plausible radicals of 1 and 2.
Scheme 2
Scheme 2
Proposed coupling mechanism of compounds 3 and 11.
Scheme 3
Scheme 3
Proposed coupling mechanism of compounds 4–10.
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