Dr Paul Evans B.Sc., D.Phil
Contact Details
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Biography:
B. Sc. (1994), University of East Anglia; D. Phil. (1998), University of York in synthetic organic chemistry (supervisor, Prof. R. J. K. Taylor); Postdoctoral work (1998-2001) in the areas of transition metal mediated synthesis and medicinal chemistry, University of Leeds (Prof. R. Grigg) and University of Manchester (Prof. E. J. Thomas); Charterhouse Lecturer in Organic and Medicinal Chemistry (2001-2003), University of Liverpool; Lecturer in Organic and Medicinal Chemistry (2003-2006), Trinity College Dublin; Current position: Lecturer in Organic Chemistry, University College Dublin. |
Research Interests
| Our research focuses on the development of new synthetic methods for the preparation of compounds whose particular structural characteristics indicate potential biological properties. One of the main themes has been the preparation of cross- conjugated cyclopentenones that featured a one-pot conjugate addition Peterson-olefination sequence (see Figure 1). This method enables the rapid construction of compounds related to Δ12,14-15-deoxy-PGJ2, a member of the well-known prostaglandin family of natural products. These compounds exhibit several interesting biological activities, including the inhibition of NF-kB, and both activation of the heat shock response (mediated by heat-shock proteins) and peroxisome proliferator activated receptor-γ (PPAR-γ). The latter transcription factor is involved in the way the body uses fats and glucose and is the molecular target for a class of drugs marketed for the treatment of type-2 diabetes. We are involved in a programme whose aim is to prepare and evaluate using a high throughput assay a library of cross-conjugated cyclopentenones for their activation of PPAR-γ.
We have also developed a highly efficient method for the preparation of novel enantio enriched cyclopentenones employing the lipase enzyme Novozyme 435® as a means to discriminate between mirror image forms of molecules (Figure 2). The ultimate aim of this project is to use these compounds as synthetic building blocks for the preparation of cross conjugated cyclopentenones as a single mirror image form. More recently we have developed an efficient and mechanistically interesting method for the preparation of cyclic aryl amines involving the double reduction of cyclic sulfonamides (Figure 3). Aromatic amines, accessible using this methodology, are structurally related to neurotransmitters like nicotine and dopamine. We aim to use this reaction for the stereoselective preparation of amino containing alkaloids like lasubine I. |
Book Chapters
| Y. Kavanagh and P. Evans; (2007) 'Pauson-Khand Reaction in the Synthesis of N- and O-Heterocycles' In: T. S. Kaufman and E. L. Larghi (eds). Modern Approaches to the Synthesis of O- and N- Heterocycles Vol 2. Trivandrum - 695023, Kerala, India: Research Signpost. [Details] |
Peer Reviewed Journals
| Morgan BS, O'Byrne A, Murray C, Keegan D, Palacio C, Evans P, ; (2010) 'The thio-adduct facilitated, enzymatic kinetic resolution of 4-hydroxycyclopentenone and 4-hydroxycyclohexenone'. Organic and Biomolecular Chemistry, 8 (3):539-545. [DOI] [Details] |
| Evans P, Klein JE, Geoghegan K, Méral N, ; (2010) 'Selective generation of quaternary all-carbon-centres through Heck-cyclisations: synthesis of mesembrane'. Chemical Communications, 46 (6):937-939. [DOI] [Details] |
| Evans P, McLaughlin NP, ; (2010) 'Dihydroxylation of vinyl sulfones: stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone'. Journal of Organic Chemistry, 75 (2):518-521. [DOI] [Details] |
| Evans P, Kelleher S, Quesne PY, ; (2009) 'Diastereoselective functionalisation of benzo-annulated bicyclic sultams: Application for the synthesis of cis-2,4-diarylpyrrolidines'. Journal of Organic Chemistry, 5 . [DOI] [Details] |
| Evans P, Klein JE, Müller-Bunz H, ; (2009) 'Studies concerning the electrophilic amino-alkene cyclisation for the synthesis of bicyclic amines'. Organic and Biomolecular Chemistry, 7 (5):986-995. [DOI] [Details] |
| P. Evans, A. T. L. Lee and E. J. Thomas; (2008) 'Synthesis of a 6-Aryloxymethyl-5-hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-one: a Muscarinic (M3) Antagonist'. Organic and Biomolecular Chemistry, 6 (12):2158-2167. [Details] | |||||||||
| B. Bradshaw, P. Evans, J. Fletcher, A. T. L. Lee, P. G. Mwashimba, D. Oehlrich, E. J. Thomas, R. H. Davies, B. C. P. Allen, K. J. Broadley, A. Hamrouni and C. Escargueil; (2008) 'Synthesis of 5-Hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-ones; Selective Antagonists of Muscarinic (M3) Receptors'. Organic and Biomolecular Chemistry, 6 (12):2138-2157. [Details] | |||||||||
| A. O¿Byrne and P. Evans,; (2008) 'Rapid synthesis of the tetrahydroquinoline alkaloids; angustureine, cuspareine and galipinine'. Tetrahedron, 64 (35):8067-8072. [Details] | |||||||||
| M. J. Stefanko, Y. K. Gun¿ko and P. Evans; (2008) 'Synthesis of Functionalised Polyethylene Glycol Derivatives of Naproxen for Biomedical Applications'. Tetrahedron, 64 (44):10132-10139. [Details] | |||||||||
| M. Iqbal, P. Duffy, G. Cloughley, B. Allan, P. Evans, X. Verdaguer, A. Riera and A. Lledó; (2008) 'The Conjugate Addition/Peterson Olefination Reaction for the Preparation of Cross-Conjugated Cyclopentenone, PPAR-g Ligands'. Organic and Biomolecular Chemistry, . [Details] | |||||||||
| Y. Kavanagh, C. M. Chaney, J. Muldoon and P. Evans; (2008) 'Iridium Catalyst Mediated Isomerisation-Cyclisation of Pauson-Khand Derived Bicyclic Allylic Alcohols'. Journal of Organic Chemistry, 73 . [Details] | |||||||||
| J. Klein, H. Müller-Bunz, Y. Ortin and P. Evans; (2008) 'Formation of Cyclic Sulfonamides via an Unusual 8-endo -trig Heck Olefination Reaction0'. Tetrahedron Letters, 49 . [Details] | |||||||||
| Byrne, S. J., le Bon, B., Corr, S. A., Stefanko, M., O'Connor, C., Gun'ko, Y. K., Rakovich, Y. P., Donegan, J. F., Williams, Y., Volkov, Y., Evans, P. ; (2007) 'Synthesis, Characterisation, and Biological Studies of CdTe Quantum Dot-Naproxen Conjugates'. ChemMedChem, 2 . [Details] | |||||||||
| Evans, P. ; (2007) 'The Double Reduction of Cyclic Sulfonamides for the Synthesis of (4S-Phenylpyrrolidin-4R-yl)methanol and 2S-Methyl-4S-phenylpyrrolidine'. Journal of Organic Chemistry, 72 . [Details] | |||||||||
| Banide E. V., Müller-Bunz H., Manning A. R., Evans P. and McGlinchey M. J. ; (2007) 'X-Ray Crystal Structure of an Unprecedented Alkene-Pentacarbonyldicobalt-Alkyne Complex: First Isolation of a Stable Magnus-Type Pauson-Khand Reaction Intermediate'. Angewandte Chemie International Edition, 46 . [Details] | |||||||||
| Kelleher, S., Muldoon, J., Müller-Bunz, H. and Evans, P.; (2007) 'Studies concerning the double reduction of Diels'Alder derived bicylic sulfonamides'. Tetrahedron Letters, 48 . [Details] | |||||||||
| Morgana, BS; Roberts, SM; Evans, P; ; (2006) 'Enzymatic kinetic resolution of 1,1-dioxo-2,3-dihydro-1H-1 lambda(6)-thiophen-3-ol via temporary derivatisation'. Tetrahedron Letters, 47 (30):5273-5276. [Details] | |||||||||
| Evans, P., Johnson, P. Taylor, R. J. K.; (2006) 'The Epoxy-Ramberg-Backlund Reaction (ERBR): A Sulfone Based Method for the Synthesis of Allylic Alcohols'. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, . [Details] | |||||||||
| Evans, P., McCabe, T., Morgan, B. S. and Reau, S.; (2005) 'The Double Reduction of Cyclic Aromatic Sulfonamides: A Novel Method for the Synthesis of 2- and 3-Aryl Substituted Cyclic Amines'. ORGANIC LETTERS, . [Details] | |||||||||
| Iqbal, M; Evans, P; Lledo, A; Verdaguer, X; Pericas, MA; Riera, A; Loeffler, C; Sinha, AK; Mueller, MJ; ; (2005) 'Total synthesis and biological activity of 13,14-dehydro-12-oxo-phytodienoic acids (deoxy-J(1)-phytoprostanes)'. Chembiochem, 6 (2):276-280. [Details] | |||||||||
| J. F. Bickley, A. Ciucci, P. Evans, S. M. Roberts, N. Ross and M. G. Santoro; (2004) 'Reactions of some Cyclopentenones with Selected Cysteine Derivatives and Biological Activities of the Product Thioethers'. BIOORGANIC AND MEDICINAL CHEMISTRY, . [Details] | |||||||||
| M. Iqbal, Y. Li and P. Evans; (2004) 'Synthesis of Δ12,14-15-Deoxy-PG-J1 Methyl Ester and epi-Δ 12-15-Deoxy-PG-J1'. TETRAHEDRON, . [Details] | |||||||||
| B. S. Morgan, D. Hoenner, P. Evans and S. M. Roberts; (2004) 'Facile Biocatalytic Syntheses of Optically Active 4-Hydroxycyclohex-2-enone and 4-Benzylthiacyclopent-2-enone'. Tetrahedron: Asymmetry, . [Details] | |||||||||
| M. Iqbal and P. Evans; (2003) 'Conjugate Addition-Peterson Olefination Reactions: Expedient Routes to Cross Conjugated Dieneones'. TETRAHEDRON LETTERS, . [Details] | |||||||||
| P. Evans and M. Leffray; (2003) 'Asymmetric Dihydroxylation of Vinyl Sulfones: Routes to Enantioenriched α-Hydroxyaldehydes and the Enantioselective Syntheses of Furan-2(5H)-ones'. TETRAHEDRON, . [Details] | |||||||||
| M. Iqbal, N. Vyse, J. Dauvergne and P. Evans; (2002) 'Microwave Promoted Pauson-Khand Reactions'. TETRAHEDRON LETTERS, . [Details] | |||||||||
| P. Evans, R. Grigg and M. York; (2000) 'Ring Closing Metathesis Reactions of Isoquinoline and β-Carboline Enamines'. TETRAHEDRON LETTERS, . [Details] | |||||||||
| P. Evans and R. J. K. Taylor; (1997) 'Novel Tandem Conjugate Addition-Ramberg-Bäcklund Rearrangements'. SYNLETT, . [Details] | |||||||||
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