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.
Highlights
Stilbene dimers with indane skeletons possess a wide range of biological activity [1,2] and novel structures which are difficult to achieve by common organic reactions on account of their intricate architectures and chiral centers
In our previous paper [13], we reported that the transformation of isorhapontigenin (2) with K3Fe(CN)6/sodium acetate (NaOAc) as oxidant yielded shegansu B (3) as the major product peak (65.2%) and another peak according to high-performance liquid chromatography (HPLC)
The oxidative coupling reaction of isorhapontigenin and resveratrol with K3Fe(CN)6/NaOAc in aqueous acetone as oxidant, in combination with silica gel column chromatography and preparative Rp-HPLC resulted in the isolation of nine stilbene dimers
Summary
Stilbene dimers with indane skeletons possess a wide range of biological activity [1,2] and novel structures which are difficult to achieve by common organic reactions on account of their intricate architectures and chiral centers. As many of these compounds are exclusively obtained by extraction from natural sources, the studies of biological properties are limited by their extreme scarcity. This has made the synthesis of stilbene dimers, especially indane dimers a popular research topic [3]. K3Fe(CHNO )6/NR1aOAc as oxidant, the isR1olation and structural identification of the products, and the discuss4iaon of the mechanisms of formatioOnH of all the products
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