Studies On The Construction Of C-C Bond And Synthesis Of Lycopodine Alkaloid

The thesis describes the studies on "Construction of C-C bond and Synthesis of Lycopodine Alkaloid", including mainly the following four parts.1. An efficient iron(â…¢)-catalyzed three component coupling of aldehyde, alkyne and amine to synthesis of propargylamines has been developed. This method has proved to be applicable to a wide range of substrates, including aromatic/aliphatic aldehydes, aromatic/aliphatic alkynes, and cyclic/acyclic secondary amines.2. An efficient iron(â…¢)-catalyzed three component coupling of aldehyde, alkyne and aniline to synthesis of substituted quinolines has been developed for the first time. This reaction proceeds under mild conditions, which provided a new route for synthesis of substituted quinolines. A cooperative coupling/hydroarylation process was also proposed.3. The intramolecular Schmidt reaction has been explored. Starting from the 1, 3-cyclopentane, the key Schmidt reaction was realized through 11 steps, however, we found 5-7-6 tricycle skeleton was formed instead of the desired 6-6-6 skeleton. A possible process was proposed based on the result.4. Palladium catalyzed direct arylation of benzoxazole using simple unactivated arenes as coupling partner has been developed for the first time. Using unactivated arenes as coupling partner other than the halides or its equivalents used in the traditional coupling reaction, the C-C bond formation was realized in the presence of oxygen as co-oxidant. This is a new bond forming mode and a highly atom-economic transformation. Mechanism investigation showed that this transformation is underwent a dual C-H activation including electrophilic aromatic substitution and concerted metalation-deprotonation process.