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The synthesis of taxol and analogies via cation-mediated cascade cyclisation

Objective



The Taxol family of molecules has commanded the attention of the most important synthetic organic chemists due to their unusual tetracyclic structure and, more importantly, to their potent anti-cancer properties. In this project it is intented to develop a new synthetic strategy towards this family of compounds, in which two major fragments are coupled at a late stage in the sequence, and Band C-rings are cyclised in a single step via cation-mediated cascade cyclisation. The cyclohexenyl A-ring acts as a spacer group between the oxetane D-ring acetal and the nucleophilic propargylic silane terminator.
The termodynamic driving force for the sequential C-C bond formation will be as a result of formation of increasingly stabilised carbocationic species down the cascade. The novelty of this strategy lies in the cyclisation of a precursor containing intact A and D rings to form B and C rings.

Funding Scheme

RGI - Research grants (individual fellowships)

Coordinator

IMPERIAL COLLEGE OF SCIENCE, TECHNOLOGY AND MEDICINE
Address
South Kensington
SW7 2AZ London
United Kingdom

Participants (1)

Not available
Spain