Benzene - Type Oligomeric Stilbene Derivatives

Oligostilbenes, a new type of natural products, were greatly developed in the past 30 years, and more than 500 stilbene oligomers were isolated as natural products till today. It is reported that these oligomers showed various biological activites, such as anti-inflammatory, anti-oxidant, anti-tumor, anti-Alzheimer, and so on. As one of important oligomeric stilbenes, indane derivatives are attracting more and more attention of researchers from all over the world because of their diverse and potent activities. However, complex structures and difficulties of synthesis for naturally occurring oligostilbenes make it difficult to obtain sufficient samples for further structural modification and pharmacological activity research. Therefore, with metal oxidant, enzyme, inorganic acid or organic acid as polymerization agent, biomimetic synthesis through oxidative coupling reaction is an effective way to obtain the oligomers.The thesis summarized the biological activities of indane derivative based on reading of a number of literatures, which provides useful references for the further research on indane derivatives.Oxidative coupling reaction of resveratrol in aqueous acetone with K3Fe(CN)6/NaOAc as oxidant resulted in the isolation of 6 resveratrol dimer derivatives, and their structures were identified by spectroscopic analysis. The main product benzofuran dimer Rs-1 as well as the other four indane stereoisomer derivatives of resveratrol dimer were obtained in the reaction.Oxidative coupling reaction of oxyresveratrol in aqueous methanol with K3Fe(CN)6/ NaOAc as oxidant resulted in the isolation of 5 resveratrol dimer derivatives, and the structures of 4 products were identified on the basis of spectral analysis, respectively. Among them, two compounds belong to a pair of oxyresveratrol dihydrobenzofuran dimer derivatives, and the other two compounds belong to a pair of oxyresveratrol dimer derivatives with indane skeleton. The oxyresveratrol dihydrobenzofuran dimer derivatives were obtained for the first time through the method of oxidative coupling reaction.With K.3Fe(CN)6/NaOAc as oxidant, oxidative coupling reaction of stilbene dimer in an aqueous solvent mainly produced two types of stilbene dimer structure:benzofuran dimer and indane dimer. The reaction conditions mainly generated stilbene dimers were proved to be mild and controllable, which is promising to be used as a convenient method for preparing indane derivatives.