Investigation of novel thermal cyclisation reactions and studies on their application to the synthesis of selected natural products

The primary goal of this research project was to investigate the mechanism of a novel thermally activated cyclisation reaction discovered by Parsons et al. During these studies two novel reactions were discovered: For reaction see Abstract in pdf Reagents and Conditions: (i) Toluene 0.1M, reflux, 4h, 32%. For reaction see Abstract in pdf Reagents and Conditions: (i) Toluene, 0.01M, reflux, 4h, 53% Radical and ene pathways for the generation of these products were proposed. However, despite extensive empirical studies, no definitive proof for either mechanism was found. The breadth of the synthetic utility of the above reactions was also investigated by synthesizing various analogues. The general application of the Parsons’ cyclisation to the synthesis of steroid cored and the complex natural product Jiadifenin was also investigated. Advanced intermediates were synthesised and invaluable information on reactivity was gained, however these investigations could not be completed due to time constraints