Research Guides

 

Research

Our research interests are as follows: total synthesis, structure determination and methods development. We are interested in: the development of key reaction methodology, especially in the areas of oxidative radical cyclisations and transition metal catalysed processes; all aspects of the structure and conformational preferences of ring compounds; and the use of biosynthesis and computational methods as predictive tools for the structure determination of complex molecules. All of the above inform and guide our research on complex molecule total synthesis.

Synthetic Methodology

The development of new synthetic methodology is a key area of our research.  We have a keen interest in oxidative transformations which result in a significant increase in molecular complexity and functionality from substrate to product.  We have developed a number of oxidative radical reactions and the sequencing of these radical reactions with subsequent ionic reactions allows the formation of complex molecular architectures from readily accessible substrates.  We develop transition metal catalysed methodology primarily using palladium and zinc.  These methodologies result in stereocontrolled synthesis of complex, functionalised molecular building blocks for use in the synthesis of biologically important molecules.  

Structure Determination

Recently computational methods for the calculation of spectroscopic properties of organic molecules have emerged as powerful tools for structure determination and structure confirmation. In collaboration with Dr Jonathan Goodman (University of Cambridge) and Prof. Robert Paton (University of Oxford), we are using total synthesis as a tool to fully test these methods with highly flexible, computationally demanding molecules, such that all organic chemists may confidently use this technique as an aid for structure determination. 

 

Total Synthesis

Natural products continue to provide an important source of chemical entities for the treatment of human disease.  We use biologically active natural products as a source of inspiration for chemical methods development, to test our developed synthetic methodology and as important targets for total synthesis.  A selection of current and completed targets are shown.

Our research is supported by a number of pharmaceutical companies and provides an excellent training in all aspects of organic synthesis.

Selected Publications

‘Diastereoselective Synthesis of Fused Lactone-Pyrrolidinones; Application to a Formal Synthesis of (−)-Salinosporamide A’ A. W. J. Logan, S. J. Sprague, R. W. Foster, L. B. Marx, V. Garzya, M. S. Hallside, A. L. Thompson, J. W. Burton, Org. Lett. 201416, 4078.

Structure Reassignment of Laurefurenynes A and B by Computation and Total Synthesis’ D. J. Shepherd, P. A. Broadwith, B. S. Dyson,  R. S. Paton, J. W. Burton​, Chem. Eur. J.201319, 12644.

‘Total synthesis and structure confirmation of elatenyne: success of computational methods for NMR prediction with highly flexible diastereomers’ B. S. Dyson, J. W. Burton, T. I. Sohn, B. Kim, H. Bae, D. Kim, J. Am. Chem. Soc., 2012, 134, 11781.

‘Manganese(III) Acetate Mediated Oxidative Radical Cyclizations. Toward Vicinal All-Carbon Quaternary Stereocenters’ A. W. J. Logan, J. S. Parker, M. S. Hallside, J. W. Burton, Org. Lett., 2012, 14, 2940.

‘A Zinc(II) catalyst system for the Conia-ene reaction of alkynyl aminomalonates applicable to 5-endo-dig reactions’ submitted July 9th, 2011, W. Hess and J. W Burton, Adv. Synth. Catal., 2011, 353, 2966.

‘Palladium-catalyzed cyclization of N-alkynyl aminomalonates’ W. Hess, J. W. Burton, Chem. Eur. J., 2010, 16, 12303. 

‘Total synthesis of 7,11-cyclobotryococca-5,12,26-triene using an oxidative radical cyclization as a key step’ J. J. Davies, T. M. Krulle, J. W. Burton, Org. Lett., 2010, 12, 2378.

‘Manganese(III)-mediated oxidative free-radical cyclisations of allenyl malonates’ L. Curry, M. S. Hallside, L. H. Powell, S. J. Sprague, J. W. Burton, Tetrahedron, 2009, 65, 10882 - invited article.

‘Clarification of the Stereochemical Course of Nucleophilic Substitution of Arylsulfonate-Based Nucleophile Assisting Leaving Groups’ D. C. Braddock, R. Pouwer, J. W. Burton, P. Broadwith, J. Org. Chem., 2009, 74, 6042.

‘Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscula’ H. M. Sheldrake, C. Jamieson, S. I. Pascu, J .W. Burton, Org. Biomol. Chem., 2009, 7, 238 - cover article.

‘Stereostructure Assignment of Flexible Five-Membered Rings by GIAO 13C NMR Calculations: Prediction of the Stereochemistry of Elatenyne’, S. G. Smith, R. S. Paton, J. W. Burton, and J. M. Goodman, J. Org. Chem., 2008, 73, 4053.

‘Oxidative radical cyclisations for the synthesis of γ-lactones’ L. H. Powell, P. H. Docherty, D. G. Hulcoop, P. D. Kemmitt and J. W. Burton, Chem. Commun., 2008, 22, 2559.

Professor Jonathan Burton

Associate Professor of Organic Chemistry

Chemical Research Laboratory

jonathan.burton@chem.ox.ac.uk

Telephone: 01865 285 119

Research Group Website

http://research.chem.ox.ac.uk/jonathan-burton.aspx