Calebin A

Chemical Name: 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid 4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-butenyl ester
CAS No. 336784-82-8 (E-isomer)
项目整合开发状态: Biological Testing
项目研究机构: University of Illinois at Chicago (Originator)
合成路线:Vanillin (I) was protected as the tetrahydropyranyl ether (II) by treatment with dihydropyran in the presence of pyridinium p-toluenesulfonate.Similarly,hydroxyacetone (III) was converted to the corresponding tetrahydropyranyl ether (IV).Aldol condensation between aldehyde (II) and ketone (IV) using LDA in cold THF furnished the hydroxy ketone (V).Removal of the tetrahydropyranyl protecting groups of (V) under acidic conditions caused the dehydration of the beta-hydroxyl group,affording the unsaturated ketone (VI).The phenolic hydroxyl group of (VI) was then protected as the trimethylsilyl ether (VII).After protection of the phenolic hydroxyl group of ferulic acid (VIII) as the silyl ether (IX),coupling between (IX) and (VII) by means of DCC and DMAP provided the silyl-protected ester (X).This was finally desilylated by treatment with HOAc in aqueous THF.