Natural Polyhydroxy (lv, S) Synthesis

Stilbenes is the general name of a type of compounds which contain skeleton of 12- diphenyl ethene or its polymers. Polyhydroxystilbenes(PHS), the stilbenes which possesses a few phenolic hydroxy group, exists in many plants , can help to resist plants diseases, and thus is called photoalexen. In recent years , many reports about the biological activities of PHS can be seen , including antibacterium , antioxidation , antiplatelet aggregation modulation of lipid metabolism, antitumor activity and so on. For this reason, PHS has taken extensive attention and is being studied continuously nowadays . Resveratrol , one of PHS, is the focus of the attention for its outstanding biological activities and excellent prospect in application. For the limited natural resources of PHS has restricted the research about its activities and applications, it becomes much more important to search for the synthetic methods for preparation of PHS . By far , there are not too much research on PHS?synthesis in the world and no relevant report can been seen in domestic publications . With reference to the related foreign literatures, we have investigated the method for resveratrol synthesis in this paper. According to the designed routine, we synthesized the target compound starting with a drug immediate ,5-dihydroxybenzyl alcohol , which undergoes five steps including methylation , bromidation , Arbuzov rearrangment , Wittig-Homer reaction and demethylation with an overall yield of 19. 7% .This routine is reasonable and applicable for the synthesis of resveratrol with available regents , mild condition and shorter steps comparedto foreign published methods .The final synthesized production was characterized as trans- 3, 5, 4 trihydroxystilbene by means of spectra determination including 1H-NMR ,C- NMR ,-1H COSY ,1H-C COSY and Long Range 1H-C COSY . All data were identical with that in literature. Meanwhile we also simply discussed the problems in protecting phenoic hydroxy and removing protective groups , the solvent effects in methylation of phenol , the method for bromidation of alcohol , the influencing factor in Wittig-Homer reaction and demethylation reaction . The synthetic method and routine for resveratrol would be the foundations of synthesis and applications for other PHS.