Studies On Total Synthesis Of (+)-Conagenin And (+)-Furanomycin And Copper(â… )-catalyzed Cascade Reactions

The thesis aims at the studies on Asymmetric synthesis of (+)-Conagenin and(+)-Furanomycin and Copper(I)-catalyzed cascade reactions for the direct synthesis of2-methylenepyrrolidinesPartⅠAsymmetric synthesis of natural product (+)-ConageninIntroduced the progress in the total synthesis of natural product (+)-Conagenin andisomers. Taking most advantage of successful methods of synthesizing or-amino acids,we applied tricyclic iminolactones into the total synthesis of natural product(+)-Conagenin and designed a short practicable route that the methyl (S)-methylserinewas synthesized starting from them for 4 steps with high diastereoslective and highyield.PartⅡAsymmetric synthesis of natural product (+)-FuranomycinIntroduced the progress in the total synthesis of natural product (+)-Conagenin andisomers. After finishing the total synthesis of natural product (+)-Conagenin, we triedto synthesis the other natural product (+)-Furanomycin. A reasonable route wasdesigned to finish it by exploiting the rule of tricyclic iminolactones and aromatic oraliphatie aldehyde. Now, we have prepared theα,β-unsaturated aldehyde(Z/E=44:1)and the aldol product in high selectivity.PartⅢCopper(I)-catalyzed cascade reactions for the direct synthesis of2-methylenepyrrolidinesIntroduced the progress in the synthesis of pyrrolidine derivatives and extended tostudy on the reaction. We have developed an efficient method for the synthesis of2-methylenepyrrolidines through base and copper(I)-catalyzed Mannich,hydroamination cascade reaction. What's more, a rational mechanism has beenproposed by deeply studies the reaction process.PartⅣCopper(I)-catalyzed reactions for the direct synthesis of 2-methylene-dihydrofuransTaking most advantage of successful methods for the synthesis of2-methylenepyrrolidines through base and copper(I)-catalyzed Mannich,hydroamination cascade reaction, we have also developed an efficient approach forthe synthesis of 2-methylene-dihydrofurans. The reaction is believed to have a goodregioselectivity and rate with small amount of catalyst.