The Studies On The Synthesis Of Resveratrol Analogues And Ramification

Stilbene which exsit in nature is called the antitoxin of palnt. It is produced by palnt's immune system when it came in for infraction from environment and get much attention because of its various physiological activity. As one of Stilbene's monomer , resveratrol analogues and ramification have many important physiological activity. Such as : anticancer,anti-agednessdementia, antioxidation and so on. Because of its's medical chemistry develop quickly and durative update on effect position. It become a kind of molecule which is good for us to pay much attention on the domain of medical chemistry.There are some pivotal point at the Synthesis of resveratrol analogues and ramification: First, How to construct the ethylene bridge; Second, How to choose the substituent's category and position which possibly have potential physiological activity. Third, How to get simplex configurational ethylene bridge, especially the (E-) configuration.Although there are many methods can be used to synthesize resveratrol analogues and ramification, the great mass of methods have many limitation such as highly cost, rigorous reaction condition and so on. So ,It is very important to find a lowly cost and gentle reaction condition approach. Under this instructional thinking, we have done some work as follow:1. There has been designed a synthetical route whose core is the reaction of Wittig-Horner, choose (E-) configuration as the basic frame of resveratrol analogues and ramification and via a series of molecule's modify to obtain target compound.2. Use low-cost Gallic acid for raw material via methylation, deoxidized by LiAlH4, bromization, Arbuzov-recomposition, Wittig-Horner reaction and so on to obtain five compounds of 7a～7e.3. Use low-cost Gallic acid for raw material via single methylation, molecule's interior condensation, deoxidized by LiAlH4, bromization, Arbuzov-recomposition, Wittig-Horner reaction and so on to obtain two compounds of 14a,14b.4. Choose resveratrol analogues of compound which have'–OH'to react with Dimethylallyl bromine and Farnesyl bromine to obtain five the ramification of resveratrol analogues: 8a,8b,8c,8d,15a. .5. Study on the reaction condition in synthesis route, optimized the reaction condition(such as molar proportion, reaction temperature, the order of reagent's addition and so on ) , approve the reaction yield ,The whole yield achieve30～35%. All of the synthesized compounds have been confirmed by ~1H NMR, MS, IR.