Study On The Synthesis Of Three Kinds Of Active Natural Products

Kinsenoside and goodyeroside A, two epimers of plant natural products withdiverse biological activities, have been synthesized efficiently by a combination ofchemical and enzymatic approaches with a total yield of12.7%. Firstly, the twoenantiomers of the aglycon,3-hydroxy-γ-butyrolactone, were prepared from D/L-malic acids by a chemical approach in a yield of75.2%within four steps. Secondly,3-hydroxy-γ-butyrolactones were successfully converted to their glycosides in thepresence of β-D-glucose by using β-D-glycosidase from almond as a catalyst in ahomogeneous organic-water system. Thirdly, a method for the determination ofkinsenoside and goodyeroside A was developed by HPLC with ELSD. Finally,single-factor and orthogonal experiments were employed to confirmed the influencesof reaction time, enzyme dosage and concentration of3-hydroxy-γ-butyrolactone onthe yield of product. Under the optimized enzymatic conditions, the yields ofkinsenoside and goodyeroside A reached17%and16.8%respectively.ZHAO330, a new compound separated from Salvia przewalskii Maxim, is acomplicated derivative of abietane type diterpene and shows significant anti-tumoractivity in vitro cytotoxicity experiment. This topic with a total synthesis routedesigned for ZHAO330has explored the synthesis of substituted phenanthrene andthe introduction of chiral lateral chain. Firstly, with3,4-dihydroxybenzaldehyde asraw materials, substituted phenanthrene was synthesized in six steps. Then, throughusing different protecting groups, phenolic hydroxyl on phenanthrene was substitutedselectively, which would lay the foundation for the synthesis of lateral chain.