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

Faggiani, Davide (2012) Investigation of novel thermal cyclisation reactions and studies on their application to the synthesis of selected natural products. Doctoral thesis (PhD), University of Sussex.

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Abstract

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:

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Reagents and Conditions: (i) Toluene 0.1M, reflux, 4h, 32%.

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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

Item Type: Thesis (Doctoral)
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry > QD0241 Organic chemistry
Depositing User: Library Cataloguing
Date Deposited: 14 Jan 2013 06:55
Last Modified: 08 Sep 2015 13:34
URI: http://sro.sussex.ac.uk/id/eprint/43296

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