Chapter one presents an account of the isolation and structure determination of thapsigargin and related natural products. Chemical manipulations of the natural product skeleton are discussed. Chapter two details the biological activity of the natural product. The structure-activity relationships are also described. Chapter three introduces the synthetic plan for thapsigargin, incorporating a Prins reaction to generate the hydroazulene skeleton of the natural product. Chapter four describes a revised synthetic strategy, based upon a ring closing metathesis reaction. Attempts to install the stereochemistry at C-10 in thapsigargin with improved selectivity are discussed. Chapter five describes the developments of a model system to study the proposed end-game in the synthesis of thapsigargin. Chapter six provides a formal account of the experimental procedures, and the appendices contain supporting information (X-ray Crystallographic data and selected NMR spectra).
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:598085 |
| Date | January 2004 |
| Creators | Cowburn, C. J. |
| Publisher | University of Cambridge |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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