Wilkes, Antonia (2015) Towards the synthesis of the ABC tricycle of Taxol. PhD thesis, University of Glasgow.
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Abstract
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.
Item Type: | Thesis (PhD) |
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Qualification Level: | Doctoral |
Keywords: | Taxol Synthesis Tricycle Ring Closing Metathesis |
Subjects: | Q Science > QD Chemistry |
Colleges/Schools: | College of Science and Engineering > School of Chemistry |
Supervisor's Name: | Prunet, Dr. J. |
Date of Award: | 2015 |
Depositing User: | Miss A Wilkes |
Unique ID: | glathesis:2015-5885 |
Copyright: | Copyright of this thesis is held by the author. |
Date Deposited: | 07 Jan 2015 08:30 |
Last Modified: | 07 Jan 2015 09:44 |
URI: | https://theses.gla.ac.uk/id/eprint/5885 |
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