| The present dissertation summarized the common structure and application of resveratrol which is a stilbenoid, a type of natural phenol, and its synthetic ways. The unprecedented compound, 5-[(1E)-2-[3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]ethenyl]-1,3-dimethoxybenzene was designed and synthesized in 49.1% overall yield based on the starting material methyl 3,4,5-trihydroxybenzoate. The synthetic procedure was commenced with the selective methylation to provide methyl 3,4,5-trihydroxybenzoate via protection and deprotection. After several transformations one of the key intermadiate 3-((tert-butyldimethylsilyl)oxy)-4-methoxy-5-((trimethylsilyl)oxy)benzaldehyde was prepared. Another key precursor, diethyl 3,5-dimethoxybenzylphosphonate, was obtained from 3,5-dimethoxybenzaldehyde. The present protocol carries several advantages including no use of any expensive and hazardous reagents like DMF, chloroform, purifying the product through recrystallization and beating to avoiding column chromatography. Thus, a reliable process suitable to industry manufactory has been developed. |
