Studies On The Arylation And Vinylation Of Alkenes And The Synthesis Of Lycopodium Alkaloids

The thesis aims at the studies "Arylation and Vinylation of Alkenes Based on Unusual Sequential Semipinacol Rearrangement/Grob Fragmentation of Allylic Alco-hols and the total synthesis of Sieboldine A and Fawcettimine of Lycopodium alkaloids" and includes two parts:Part I:Alkenes can be stereoselectively arylated and vinylated without transition-metal catalyst under mild conditions through an interesting NBS-promoted semipinacol rearrangement and a subsequent unusual NaOH-mediated Grob fragmentation. The current protocol is insensitive to oxygen and moisture, leading to a very convenient experimental manipulation. And, we gave two different reaction mechanisms for cyclic and acyclic substrates respectively.Part II:Lycopodium alkaloids are a structurally related, quinolizine and pyridine or a-pyridone type, and originally identified from Lycopodium. Initially, we aimed at the synthesis of Sieboldine A and Fawcettimine of Lycopodium alkaloids based on our own reaction methods which were "Synthesis of Chiral Spiroethers" and "Construction of Chiral All-Carbon Quaternary Stereocenters in Spirocyclic". Although many efforts have been made, we do not complete the total synthesis. But all those endeavors have afforded valuable information for the following investigations.