研究领域

Organic Chemistry

Our research interests are in catalysis and synthetic organic chemistry, and the contribution that they can make to the fields of medicine and natural products. We concentrate on developing new catalytic methodologies for synthetic organic chemistry and asymmetric synthesis and then employing our chemistry to make biologically important natural products. Our work is directly relevant to the pharmaceutical industry and the research group is supported by multi-national companies including Merck, AstraZeneca, GlaxoSmithKline, Lily, Novartis, Roche, Aventis and Pfizer. The facilities available for research in our labs in the CRL are second to none. The research group consists of four part II’s, twelve DPhil students and four postdoctoral assistants. We meet two/three times per week to discuss advances in the laboratory and hold problem sessions to highlight recent developments in the literature. We are an active and vibrant research group with a positive dynamic and friendly atmosphere. Excellent support is given to new part II’s and DPhil students in the form of mentorship by a senior group members. Our research interests are wide ranging, encompassing osmium-catalysed processes, Birch reduction of pyrroles and pyridinium salts, carbohydrate chemistry and catalytic ring closing metathesis as a strategy for the formation of aromatic heterocycles. With each new catalytic method that we develop, we are also keen to show that it is useful in total synthesis. In this regard, the group has built up significant expertise in the synthesis of natural products; some of our current targets are shown below.

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Palladium-catalyzed alpha-arylation of carbonyls in the de novo synthesis of aromatic heterocycles Harish K. Potukuchi, Anatol P. Spork and Timothy J. Donohoe Organic and Biomolecular Chemistry, 2015, in the press169 Hydrogen borrowing and interrupted hydrogen borrowing reactions of ketones and methanol, catalysed by iridium Di Shen, Darren L. Poole, Camilla C. Shotton, Anne F. Kornahrens, Mark P. Healy and Timothy J. Donohoe, Angewandte Chemie Int. Ed., 2015, 54, 1642-1645 DOI: 10.1002/anie.201410391168 Short and efficient syntheses of protoberberine alkaloids using palladium catalyzed enolate arylation Alice E. Gatland, Ben S. Pilgrim, Panayiotis A. Procopiou and Timothy J. Donohoe Angewandte Chemie Int. Ed., 2014, 53, 14555-14558. DOI: 10.1002/anie.201409164167 Love-Hate ligands for high resolution analysis of strain in ultra-stable protein:small molecule interaction Michael Fairhead, Di Shen, Louis K. M. Chan, Ed D. Lowe, Timothy J. Donohoe, Mark Howarth Bioorganic & Medicinal Chemistry, 2014, 22, 5476-5486 DOI: 10.1016/j.bmc.2014.07.029 Howarth Lab166 New methods for the synthesis of naphthyl amines; application to the synthesis of dihydrosanguinarine, sanguinarine, oxysanguinarine and (±)-maclekarpines B and C Matthew R. Tatton, Iain Simpson and Timothy J. Donohoe Chem. Commun., 2014, 50, 11314-11316 DOI: 10.1039/C4CC05209A165 De novo Synthesis of Multi-Substituted Aryl Amines using Alkene Cross Metathesis Matthew Tatton, Iain Simpson and Timothy J. Donohoe Organic Letters, 2014, 16, 1920-1923. DOI: 10.1021/ol500441q164 Rhodium-Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of Alpha-Branched Products Louis K. M. Chan, Darren L. Poole, Di Shen, Mark P. Healy and Timothy J. Donohoe Angewandte Chemie Int. Ed., 2014, 53, 761-765. Designated as a HOT paper, featured as the back cover DOI: 10.1002/anie.201307950163 Total Synthesis of the Antitumor Antibiotic (+/-)-Streptonigrin: First and Second Generation Routes for de-novo Pyridine Formation using Ring Closing Metathesis Timothy Donohoe, Christopher Jones, Anne Kornahrens, Luiz Barbosa, Louise Walport, Matthew Tatton, Michael O'Hagan, Akshat Rathi, David Baker J. Org. Chem. 2013, 78, 12338-12350. DOI: 10.1021/jo402388f162 Modular isoquinoline synthesis using catalytic enolate arylation and in-situ functionalization Ben Pilgrim, Alice Gatland, Charlie McTernan, Panayiotis Procopiou, Timothy Donohoe Organic Letters, 2013, 15, 6190-6193. DOI: 10.1021/ol4030309 Tethered Aminohydroxylation: Synthesis of the β-Amino Acid of Microsclerodermins A and B Robert D. C. Pullin , Akshat H. Rathi, Ekaterina Y. Melikhova, Christian Winter , Amber L. Thompson, and Timothy J. Donohoe Organic Letters, 2013, 15, 5492-5495. DOI: 10.1021/ol402638n160 Lithium-4,4'-Di-tert-butylbiphenylide Christopher R. Jones and Timothy J. Donohoe Encyclopedia of Reagents for Organic Synthesis, 2013159 Vinyl Weinreb Amides: A Versatile Alternative to Vinyl Ketone Substrates for Heck Arylation David B. Baker, Peter T. Gallagher and Timothy J. Donohoe Tetrahedron 2013, 69, 3690-3697. DOI: 10.1016/j.tet.2013.03.009158 Osmium-Catalyzed Oxidative Cyclization of Dienes and Their Derivatives Ben S. Pilgrim and Timothy J. Donohoe J. Org. Chem. 2013, 78, 2149-2167. Work from this paper featured in the cover picture for JOC. DOI: 10.1021/jo302719y157 Interplay of cascade oxidative cyclisation and hydride shifts in the synthesis of the ABC spiroketal ring system of pectenotoxin-4 Timothy, J. Donohoe and Radek Lipinski Angew. Chem. Int. Ed. 2013, 52, 2491-2494. Designated as a Hot Article. DOI: 10.1002/anie.201208919156 Oxidative cyclisation for the synthesis of complex THF-containing natural products Timothy, J. Donohoe, Robert D. C. Pullin, Radoslaw M. Lipinski Pure & Applied Chem. 2013, 85, 1175-1184. DOI: 10.1351/PAC-CON-12-10-25155 Partial and complete reduction of pyrroles, furans, thiophenes and their benzo-analogues and of aromatic heterocycles containing more than one heteroatom Timothy J. Donohoe,* Christopher Jones and Christian Winter Comprehensive Organic Synthesis II, Ed. G. Molander and P. Knochel, Elsevier, 2013, in the press.154 Asymmetric Synthesis of the Fully Elaborated Pyrrolidone Core of Oxazolomycin A Timothy J. Donohoe, Timothy J. C. O'Riordan, Manuel Peifer, Christopher R. Jones, Timothy J. Miles Organic Lett. 2012, 14, 5460-5463. DOI: 10.1021/ol302541j153 Natural Product Synthesis as a Challenging Test of Newly Developed Methodology Timothy J. Donohoe, Robert D. C. Pullin Chemical Commun. 2012, 48, 11924-11938 DOI: 10.1039/C2CC36040C152 Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones Timothy J. Donohoe, Ben S. Pilgrim, Geraint R. Jones and José A. Bassuto Proc. Natl. Acad. Sci. US, 2012, 109, 11605-11608. DOI: 10.1073/pnas.1206532109 A green approach to Fenton chemistry: Hydroxylation of salicylic acid in aqueous medium using electrogeneration of Fenton's Reagent Janjira Panchompoo, Leigh Aldous, Mikhail Kabeshov, Ben S. Pilgrim, Timothy J. Donohoe and Richard G. Compton New. J. Chem. 2012, 36, 1265-1272. DOI: 10.1039/C2NJ21007J Hydrogen-Bonding-Mediated Directed Osmium Dihydroxylation Timothy J. Donohoe, Carole J. R. Bataille, Paolo Innocenti Organic Reactions, 2012, 76, 1-47. DOI: 10.1002/0471264180.or076.01