The Syntheses Of Racemic Bisabolane Sequiterpenoids Compounds And Heliannuol D

The bisabolane sequiterpenoids compounds are widely distributed in nature. Many ofthem possess good biological activities,such as antibacterial, anti-virus, antitumor et al.. Forexample: Heliannuol D isolated from cultivated sunflower has strong allelopathic effects.In this thesis, we mainly focused on the syntheses of aromatic bisabolanesequiterpenoids compounds of (±)-Curcumene1,(±)-Xanthorrhizol2and (±)-Curcuhy-droquinone3, and the exploratory study of Heliannuol D.The main conclusions were as follows:Part1: P-Bromotoluene, p-toluidine and methylhydroquinone as starting materials, Weprepared their brominated aromatic compounds6b,6c. After the lithiation addition,hydrogenation reduction, the total syntheses of (±)-Curcumene1,(±)-Xanthorrhizol2and(±)-Curcuhydroquinone3was completed,verifying the structure of all above compounds byNMR, MS and IR.Part2: O-cresol as a raw material, taking the steps of methylation, acylation, Baeyer-Villigeroxidative rearrangement, hydrolysis, bromination, protection of hydroxyl group et al.,Wepossessed the brominated aromatic intermediate6d. With it in hand, Similar approaches havebeen used, we synthesized the key compounds1-10.(±)-Heliannuol D was achieved viaseveral steps such as the change protection, epoxidation, cyclization, demethylation. Theyield of the product was less than3percent. The intermediate structures were verified byNMR and MS.