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Title: Towards the synthesis of the ABC tricycle of Taxol
Author: Wilkes, Antonia
ISNI:       0000 0004 5349 215X
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 2015
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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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry