Towards the synthesis of the ABC tricycle of Taxol

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)
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: http://theses.gla.ac.uk/id/eprint/5885

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