People in the Department

Dr Gareth J Pritchard

Senior Lecturer in Organic Chemistry
BSc London(Imperial), Ph.D Wales(Swansea), ARCS.

Telephone: 01509 222586
E-mail: G.J.Pritchard@lboro.ac.uk

Gareth Pritchard's Research Group

The main areas of interest to the group are, looking for 'new' reactions, new synthetic methodology and the synthesis of highly functionalised molecules. The demand for routes to small highly functionalised molecules for biological screening, and thus new medicinal drugs, is a challenge to organic chemists. We are developing methods to meet this important challenge.

(a) Palladium Catalyzed Reactions of Vinylcycloproanes
Work currently underway has shown that vinylcyclopropanes can be ring opened, with palladium(0), and trapped with aldehydes and imines to give tetrahydrofurans and pyrrolidines respectively. We are expanding this methodology to other more complex molecules such as nonactic acid, the alkaloid monomorine, anologs of castanospermine and swainsonine. The reaction occurring under very mild conditions, room temperature and catalytic in palladium, and is tolerant of many functional groups. The methodology is a very powerful new route to these structures.

(b) Stoicheiometic Organometallic Routes to Heterocyclic systems (With Dr S. D. R. Christie)
With Dr. Christie’s group we are looking at the cycloaddition reactions strained ring systems which a activated with electron withdrawing groups and an organometallic group.

S. D. R. Christie, R. J. Davoile, M. R. J. Elsegood, R. Fryatt, R. C. F. Jones and G. J. Pritchard, J. Chem. Soc., Chem. Commun., 2004, 2474-2475.

E. A. Allart, S. D. R. Christie, G. J. Pritchard and M. R. J. Elsegood, submitted to J. Am. Chem. Soc.

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(c) Radical and Palladium Routes to Heteroaromatic and Aromatic motifs (With Professor W. R. Bowman)
Polycyclic heteroaromatic and aromatic compounds play significant role in organic compounds, and there is need for new routes to allow rapid access to know compounds and access new systems. Palladium and radical chemistry allow us methods to explore new methods to these classes of compounds.

W. R. Bowman, J. E. Lyon and G. J. Pritchard, in press, Synlett

(d) Approaches to mono-cyclic b-lactam PSA Inhibitors
Prostate specific antigen (PSA), has been extensively used as a diagnostic marker for carcinoma. PSA also exhibits proteolytic action on an insulin-like growth, which may contribute to malignant growth pf the prostate. This is a central target for medical chemistry, we are developing a range mono-cyclic b-lactam inhibitors for PSA.

P. Singh, S. A. Williams, M. H. Shah, T. Lectka, G. J. Pritchard, J. T. Isaacs and S. R. Denmeade, Proteins: Struct., Funct., Bioinfo., 2008, 70, 1416-1428.

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(e) Hypervalent Iodine Reagents
The group is also working at developing new reactions using hypervalent iodine. This involves using hypervalent iodine reagents to generate carbon base and heteroatom base reactive intermediates.

(f) Novel Nucleophilic Acylation
Acylation is an important reaction in organic chemistry, new methods of doing this reaction in a nucleophilic manner is an essential goal for organic chemists. We are looking at this reaction using both catalytic manor and stoicheiometic methods, asymmetric methods are being explored in conjuction.

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Selected publications

“Design, synthesis and proposed active site binding analysis of monocyclic 2-azetidinone inhibitors of prostate specific antigen”, R. M. Adlington, J. E. Baldwin, G. W. Becker, B. Chen, L. Cheng, S. L. Cooper, R. B. Hermann, T. J. Howe, W. McCoull, A. M. McNulty, B. L. Neubauer and G. J. Pritchard, J. Med. Chem., 2001, 44, 1491-1508.

“Total synthesis of pyridovericin: studies toward the biomimetic synthesis of pyridomacrolidin”, J. E. Baldwin, R. M. Adlington, A. Conte, N. R. Irlapati, R. Marquez, G. J. Pritchard, Organic Letters, 2002,4, 2125-2127.

“Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide”, R. M. Adlington, J. E. Baldwin, A. V. W. Mayweg and G. J. Pritchard, Organic Letters, 2002,4, 3009-3011.

“Paired electrosynthesis: micro-flow cell processes with and without added electrolyte”, C. A. Paddon, G. J. Pritchard, T. Thiemann and F. Marken, Electrochemsitry Communications, 2002, 4, 825-831.

“Novel formation and use of a Nicholas carbocation in the synthesis of highly substituted tetrahydrofurans”, S. D. R. Christie, R. J. Davoile, M. R. J. Elsegood, R. Fryatt, R. C. F. Jones and G. J. Pritchard, J. Chem. Soc., Chem. Commun., 2004, 2474-2475.

“Mechanistic Insights into the inhibition of prostate specific antigen by b-lactam class compounds”, P. Singh, S. A. Williams, M. H. Shah, T. Lectka, G. J. Pritchard, J. T. Isaacs and S. R. Denmeade, Proteins: Struct., Funct., Bioinfo., 2008, 70, 1416-1428.

“Palladium Mediated Synthesis of Phenanthridines; the First Report of Palladium Insertion into an Imidoylselanides”, W. R. Bowman, J. E. Lyon and G. J. Pritchard, in press, Synlett, 2008.