Taxol is one of the world’s most successful drugs used in the treatment of cancers. Isolated from the bark of the Pacific yew tree (Taxus brevifolia), it is a molecule of great interest within organic chemistry; with six total syntheses and a number of synthetic works having been published since its discovery. A semi-convergent synthesis of an intermediate in Holton’s synthesis was planned. The overall synthetic plan is shown below. The A ring would be installed by an intramolecular pinacol condensation. The BC bicycle would be closed by ring-closing metathesis at C10-C11. The ketone at C12 would be protected as an alkyne and the BC bicycle precursor would be obtained by coupling fragment A and the C ring. This thesis describes the preparation of a model C ring, without the oxygenated functionality at C7, was successfully synthesised along with fragment A. Metathesis precursors were synthesised and gold hydration reactions were attempted.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:634011 |
| Date | January 2015 |
| Creators | Wilkes, Antonia |
| Publisher | University of Glasgow |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://theses.gla.ac.uk/5885/ |
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