Construct Compounds Bank Of Trans-Stilbenes

Resveratrol ((E)-3,4',5-trihydroxy-stilbene), a phytoalexin found in grape skins, peanuts, and red wine, has been reported to exhibit a wide range of biological and pharmacological properties including anti-inflammatory, platelet antiaggregation, heart protection and anticarcinogenic effects.In this dissertation, we had established a facile and highly stereoselective synthetic route to analogues of resveratrol based on Heck reaction. And the influence of the catalytic system on the Heck reaction was also studied. 34 asymmetrical (E)-stilbenes were prepared efficiently using Heck reactions which were performed by reacting 12 aryl halides with 15 vinyl functional compounds. The vinyl functional compounds were prepared from corresponding arylaldehydes using Wittig reaction.McMurry coupling is an efficient reaction for construction of symmetrical (E)-stilbene derivatives. However phenolic hydroxy functionality has to be protected against rigorous conditions as methylether, resulting in later demethylation formidable and low total yield. During the course of our studies on the McMurry coupling, we found that the f-BuMe2Si protected hydroxybenzaldehydes can be subjected to the reaction sequence and all give excellent yields of symmetrical (E)-stilbenes. Using this convenient, efficient and highly stereoselective synthetic method 4 symmetrical (E)-stilbene derivatives were prepared.In this dissertation, we described a concise synthesis of both 3-O--D- and 4-0--D-glycoside conjugates of resveratrol, such that glycoside conjugates of other polyhydroxy stilbenes can be conveniently synthesized.(E)-2-styrylpyridine and (E)-2-styryl-8-hydroxyquinaldine were prepared bytreating benzaldehyde and 4-methylprydine or 8-hydroxyquinaldine respectively in refluxing DMF using KOH as the catalyst.Most of the intermediates and (E)-stilbenes were determined from spectroscopic data, such as 1H-NMR, 13C-NMR, 1H-1HCOSY, HMQC, HMBC, IR.