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The University of Southampton

Research project: Solid-Phase Organic Synthesis

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Our main contributions in the area of solid-phase synthesis have been the design of new linker strategies based on cyclisation cleavage and nucleophilic cleavage.

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We have used these ideas to develop metal-catalysed cleavage routes to pyrrolidines, allylic amines, and cyclic sulfonamides. A recent highlight in this area has been the introduction of a Resin-Linker-Vector (RLV) approach to the synthesis of medical imaging agents containing the positron-emitting isotope 18F. Medical imaging using positron emission tomography (PET) is an important technology for the diagnosis, treatment and monitoring of many diseases including cancer. In addition, this imaging modality is finding increased applications in drug development. The positron emitting isotope 18F (which has a half-life of 110 min) is widely employed in PET imaging, and we have been working in collaboration with GE Healthcare to develop 18F incorporation using the RLV approach. Advantages of the RLV strategy include easier product purification, and automation of the chemistry.

Brown, L. J.; Ma, N. C.; Bouvet, D. R.; Champion, S. M.; Gibson, A. M. R.; Hu, Y.; Jackson, A.; Khan, I.; Millot, N.; Topley, A. C.; Wadsworth, H.; Wynn, D.; Brown, R. C. D., Synthesis of the positron-emitting radiotracer [18F]-2-fluoro-2-deoxy-d-glucose from resin-bound perfluoroalkylsulfonates. Org. Biomol. Chem. 2009, 7, 564-575.
Brown, L. J.; Bouvet, D. R.; Champion, S. M.; Gibson, A. M. R.; Hu, Y. J., A.; Khan, I.; Ma, N.; Millot, N.; Wadsworth, H.; Brown, R. C. D. A solid-phase route to 18F-labeled tracers, exemplified by the synthesis of [18F]-2-fluoro-2-deoxy-D-glucose. Angew. Chem.-Int. Edit. 2007, 46, 941-944.
Meloni, M. M.; White, P. D.; Armour, D.; Brown, R. C. D. Synthesis and applications of tert-alkoxysiloxane linkers in solid-phase chemistry. Tetrahedron 2007, 63, 299-311.
Moriggi, J. D.; Brown, L. J. Castro, J. L.; Brown, R. C. D. Ring-closing metathesis: development of a cyclisation-cleavage strategy for the solid-phase synthesis of cyclic sulfonamides. Org. Biomol. Chem. 2004, 2, 835-844.
Brown, R. C. D.; Fisher, M. L.; Brown, L. J. Solid-phase synthesis of 4-methylene pyrrolidines and allylic amines using palladium-activated allylic linkers. Org. Biomol. Chem. 2003, 1, 2699-2709.

Related research groups

Organic Chemistry: Synthesis, Catalysis and Flow
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