Progress Towards The Total Synthesis Of Stemofoline

This dissertation is aiming at the synthetic study of Stemofoline, and consists of the following three parts.In chapter1, the isolation, structural characterization, biological activities, biosynthesis of the stemofoline and its analogs are summarized. The strategic approaches to the total synthesis of stemofoline are reviewed in detail.In chapter2, studies towards the total synthesis of stemofoline are described. Using the intramolecular (3+2) cycloaddition reaction of imine and donor-acceptor cyclopropane as the key reaction, we design two strategies to synthesize stemofoline.In the asymmetric strategy, we use the Evans aldol reaction and Staudinger reduction and so on to introduce most of carbon atoms and stereocenter. And do detailed research of intramolecular cyclopropanation reaction. We design to use this reaction to construct the dornor-acceptor cyclopropane stereoselcetively. Then, combine with the nucleophilic addition of amide, to synthesize the compound ready to do the intramolecular cycloaddition reaction. And wish to complete the first asymmetric total synthesis of stemofoline.In the racemic strategy, we design the double (3+2) cycloadditions of donor-acceptor cyclopropanes with nitriles to construct the aza-[5.3.0.0]-decane skeleton. In the initial research, we synthesise the1-pyrroline compounds using the methodology we developed and research the intramolecular cycloaddition in depth. This progress lays a foundation for the further research.In chapter3, the first catalytic intermolecular (3+2) cycloaddition of dornor-acceptor cyclopropanes with nitriles is described. Also on the research of the mechanism and applications.