Studies On Total Synthesis Of (+)-dihydrolyfoline(-)-5-epi-dihydrolyfoline And Ibogamine

1.Construction of chiral biaryl(review)The basic characteristics of chiral axis were summarized.And the properties of chiral biaryl axis and its constructions metholds,including substrate induction,asymmetric catalysis and racemic resolution,were summarized.2.Synthesis of(H+)-dihydrolyfoline and(-)-5-epi-dihydrolyfolineThe first asymmetric total syntheses of(+)-dihydrolyfoline and(-)-5-epi-dihydrolyfoline have been achieved.Biogenetic enzymatic oxidative couplings of phenols were used to construct the strained macrocyclic ring and the chiral biaryl axis,which realized the biogenic hypothesis proposed by Schwarting in 1971 and the oxidative coupling reactions they turned out to be impossible.The requisite quinolizidinone cores were prepared by an L-proline catalyzed Mannich reaction and an enzymatic Mannich reaction.Three generation total syntheses of(-)-5-epi-dihydrolyfoline were achieved by continuous improvements.In the six-step third-generation total synthsis of(-)-5-epi-dihydrolyfoline,five steps were catalyzed by natural catalysts.3.The study on synthesis of natural product ibogamineThe structure of natural product ibogamine was analyzed,and the previous synthesis work was reviewed.The sulfur-aza Adol/Mannich reaction strategy was designed to construct the core of ibogamine,and related research was carried out.