The proposed chemistry has been designed to provide versatile solutions to some significant problems associated with the synthesis of fluorinated products, more particularly fluorolactones. Beneficiaries of the science developed will be academics and pharmaceutical companies. The synthesis of F-organic compounds with proper functionality and favoured (drug-like) features are always of interest to pharmaceutical companies and their availability is key for successful discovery programs.
The chemistry outlined in this proposal will develop unprecedented synthetic pathways allowing for the preparation of various fluorolactones, therefore expanding the repertoire of synthetic routes to these key compounds. The chemistry builds on our interest in the use of organosilanes as starting materials for the preparation of fluorinated compounds. In this project, we will study novel synthetic routes to fluorinated heterocyclic lactones from organosilanes using two complementary strategies: the iodolactonisation of allylic fluorides and the fluorolactonisation of structurally diverse allylsilanes.
The application of this chemistry to the synthesis of a fluorinated analogue of GalNAc exemplifies how this chemistry could also contribute to the fundamental understanding of enzyme mechanism. The work will be undertaken at the University of Oxford (Chemistry, supervision Dr V. Gouverneur) by Dr M. Schuler who has recently completed her Ph D under the supervision of Professor L Ghosez (IECB).
This project will allow her to acquire expertise in fluorine chemistry but also asymmetric synthesis and silicon chemistry, therefore complementing her existing skills. The results of her work will be disseminated with publications in the form or communications and full papers and it i s anticipated that the results will be presented at national and international conferences on fluorine chemistry (oral communication and posters).
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