研究领域

Organic Chemistry

One of the main research themes of the Gouverneur’s group is Fluorine Chemistry with an extensive research programme aimed at developing novel synthetic methodologies for the preparation of fluorinated targets. Fluorine can be highly advantageous in pharmaceutical and agrochemical compounds as its presence can dramatically alter chemical and biological properties, including stability, lipophilicity and bioavailability. A recent survey has estimated that as many as 30-40% of agrochemicals and 20% of pharmaceuticals on the market contain fluorine, including half of the top drugs sold in 2005. As natural fluoroorganic compounds are extremely rare, major advances rely heavily on synthetic organic chemistry. In the group, we develop novel fluorine chemistry for the preparation of fine enantiopure fluorinated building blocks and drug-type targets. Our research programmes are designed to build knowledge on how fluorinated stereogenic centres affect drug potency and other performance compounds. The key synthetic advance emerging from our laboratories is the demonstration that organosilanes are extremely versatile precursors of a large number of fluorinated targets such as fluoroalkenes, fluorodienes, propargylic fluorides, allylic fluorides as well as fluorinated carbo- and heterocycles. A major spin-off avenue of research resulting from our activities is the preparation of [18F]-labeled radiopharmaceuticals suitable for Positron Emission Tomography (PET), a non-invasive diagnostic tool enabling the study of biochemical and physiological processes. With a half-life of circa 110 min [18F], it is critical to develop radiochemical methods featuring late introduction of the [18F] substituent within the tracer. This chemistry is designed with the aim of using PET to accelerate drug development. We are also working on the synthesis of new tracers to image hypoxia. This project is driven by the clear need in cancer treatment for a non-invasive imaging assay that evaluates the oxygenation status and heterogeneity of hypoxia and angiogenesis in individual patients. Hypoxia imaging brings in information different from that of the commonly use FDG-PET and could therefore play an important role in oncologic imaging. This specific project is carried out in collaboration with Professor John R. Dilworth (Oxford, ICL). On the 24th January 2007, a new radiochemistry laboratory equipped to handle PET and gamma emitting radioisotopes was officially opened with all the necessary equipments to carry out the synthesis of known and novel tracers. Several of the projects carried out in the Gouverneur’s group are supported by the pharmaceutical and agrochemical industry as well as leading companies engaged in imaging. See my research web site for update list of publications

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Iodine Transfer Copolymerization of Fluorinated α-Methylstyrenes with Styrene using 1-iodoperfluorohexane as the Chain Transfer Agent J. Walkowiak, A. Szwajca, F. Boschet, V. Gouverneur, B. Ameduri Macromolecules 2014, 47(24), 8634–8644 A Diversity Oriented Approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH- and CF3(SCF3)CH-Substituted Arenes from 1-(Diazo-2,2,2-trifluoroethyl)arenes E. Emer, J. Twilton, M. Tredwell, S. Calderwood, T. Collier, B. Liégault, M. Taillefer, V. Gouverneur Org. Lett. 2014, 16(22), 6004-6007 Asymmetric Fluorocyclizations of Alkenes J. Wolstenhulme, V. Gouverneur Account of Chemical Research 2014 (In Press, DOI: 10.1021/ar500282z) Anti-CD20 inhibits T cell-mediated pathology and microgliosis in the rat brain D. C. Anthony, A. M. Dickens, N. Seneca, Y. Couch, S. Campbell, B. Checa, V. Kersemans, E. A. Warren, M. Tredwell, N. R. Sibson, V. Gouverneur, D. Leppert Annals of Clinical and Translational Neurology 2014, 1 (9), 659–669 A General Copper-Mediated Nucleophilic 18F Fluorination of Arenes M. Tredwell, S. M. Preshlock, N. J. Taylor, S. Gruber, M. Huiban, J. Passchier, J. Mercier, C. Génicot, V. Gouverneur Angew. Chem. Int. Ed. 2014, 53 (30), 7751-7755 cis-Specific Hydrofluorination of Alkenylarenes under Palladium Catalysis by an Ionic Pathway E. Emer, L. Pfeifer, J. M. Brown, V. Gouverneur Angew. Chem. Int. Ed. 2014, 53 (16), 4181–4185 Glial Activation in the Early Stages of Brain Metastasis: TSPO as a Diagnostic Biomarker E. R. O’Brien, V. Kersemans, M. Tredwell, B. Checa , S. Serres, M. S. Soto, V. Gouverneur, D. Leppert, D. C. Anthony, N. R. Sibson J. Nucl. Med. 2014, 55 (2), 1-6 A Comparison of the Behaviour of 64Cu-acetate and 64Cu-ATSM in vitro and in vivo R. Hueting, V. Kersemans, B. Cornelissen, M. Tredwell, K. Hussien, M. Christlieb, A. D. Gee, J. Passchier, S. C Smart, J. R Dilworth, V. Gouverneur, R. J. Muschel J. Nucl. Med. 2014, 55 (1), 128-134 A Broadly Applicable [18F]Trifluoromethylation of Aryl and Heteroaryl Iodides for PET Imaging M. Huiban, M. Tredwell, S. Mizuta, Z. Wan, X. Zhang, T. L. Collier, V. Gouverneur, J. Passchier Nature Chemistry 2013, 5, 941-944 Enhanced Aqueous Suzuki-Miyaura Coupling Allows Site specific Polypeptide [18F]labeling M. Gao, V. Gouverneur, B. Davis J. Am. Chem. Soc., 2013, 135 (37), 13612–13615 Intramolecular OH...FC Hydrogen Bonding in Fluorinated Carbohydrates: CHF is a Better Hydrogen Bond Acceptor than CF2 G. T. Giuffredi, V. Gouverneur, B. Bernet Angew. Chem. Int. Ed. 2013, 52 (40), 10524-10528 Asymmetric Electrophilic Fluorocarbocyclization with Carbon Nucleophiles J. R. Woltenshulme, J. Rosenqvist, O. Lozano, J. Ilupeju, K. M. Engle, G. Pidgeon, P. R. Moore, G. Sandford, V. Gouverneur Angew. Chem. Int. Ed. 2013, 52 (37), 9796–9800 Redox chemistry of trifluoromethyl sulfonium salts as CF3 radical sources S. Mizuta, S. Verhoog, X. Wang, N. Shibata, V. Gouverneur, M. Médebielle Journal of Fluorine Chemistry 2013, 155, 124-131 (Special Issue in honor of Professor Ojima ACS Fluorine Award) Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes S. Mizuta, I. Stenhagen, M. O'Duill, J. Wolstenhulme, A. Kirjavainen, S. Forsback, M. Tredwell, G. Sandford, P. Moore, M. Huiban, S. Luthra, J. Passchier, O. Solin, V. Gouverneur Org. Lett. 2013, 15 (11), 2648-2651 Trifluoromethylation of Allylsilanes under Photoredox Catalysis S. Mizuta, K. M. Engle, S. Verhoog, O. Galicia-Lopez, M. O’Duill, M. Medebielle, K. Wheelhouse, G. Rassias, A. Thompson, V. Gouverneur Org. Lett. 2013, 15 (6), 1250-1253 Catalytic Hydrotrifluoromethylation of Unactivated Alkenes S. Mizuta, S. Verhoog, K. M. Engle, T. Khotavivattana M. O’Duill, K. Wheelhouse, G. Rassias, M. Medebielle, V. Gouverneur J. Am. Chem. Soc. 2013, 135 (7), 2505-2508 [18F]Fluorination of Arylboronic Ester using [18F]Selectfluor bis(triflate): Application to 6-[18F]Fluoro-L-DOPA I. S. R. Stenhagen, A. K. Kirjavainen, S. J. Forsback, C. G. Jørgensen, E. G. Robins, S. K. Luthra, O. Solin, V. Gouverneur Chem. Commun. 2013, 49, 1386-1388 Regio- and Stereoretentive Synthesis of Branched, Linear (E)- and (Z)-Allyl Fluorides from Allyl Carbonates under Ir-Catalysis E. Benedetto, M. Tredwell, C. Hollingworth, T. Khotavivattana, J. M. Brown and V. Gouverneur Chem. Sci., 2013, 4, 89-96 [Back Cover] [18F]Labeling of Arenes M. Tredwell, V. Gouverneur Angew. Chem. Int. Ed., 2012, 51 (46), 11426-11437 Synthesis of 3-Fluoropyrrolidines and 4-Fluoropyrrolidin-2-ones from Allylic Fluorides L. E. Combettes, M. Schuler, R. Patel, B. Bonillo, B. Odell, A. L. Thompson, T. D. W. Claridge, V. Gouverneur Chemistry A European Journal, 2012, 18 (41), 13126-13132