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researcher

Paul Evans

Associate Professor

School Of Chemistry
Science Centre
Belfield
Dublin 4

Tel: +353 1 7162291
Email: paul.evans@ucd.ie

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.

Publications

 

Book Chapters

K. Geoghegan and P. Evans (2013) 'Intramolecular Reactions: Formation of Carbocycles' In: M. Larhed (eds). Science of Synthesis: Cross Coupling and Heck-Type Reactions 3. Stuttgart: Thieme. [Details]
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. , pp.33-78 [Details]
 

Peer Reviewed Journals

A. Keeley, S. McCauley and P. Evans (2016) 'A Ring Closing Metathesis-Manganese Dioxide Oxidation Sequence for the Synthesis of Substituted Pyrroles'. Tetrahedron, 72 :2552-2559. [Details]
W. Doherty and P. Evans (2016) 'Aminooxylation Horner-Wadsworth-Emmons Sequence for the Synthesis of Enantioenriched g-Functionalized Vinyl Sulfones'. Journal of Organic Chemistry, 81 :1416-1424. [Details]
Tiwari U, Sheehy E, Rai D, Gaffney M, Evans P, and Cummins E. (2015) 'Quantitative human exposure model to assess the level of glucosinolates upon thermal processing of cruciferous vegetables'. LWT -- Food Science and Technology, 63 (1):253-261. [Details]
Read Zaidan, Shaun Smullen and Paul Evans (2015) 'Asymmetric synthesis of (+)- and (-)-deoxyfebrifugine and deoxyhalofuginone'. Tetrahedron Letters, 56 :6433-6435. [Details]
Cleary JA, Doherty W, Evans P, Malthouse JP. (2015) 'Quantifying tetrahedral adduct formation and stabilization in the cysteine and the serine proteases'. Biochimica et Biophysica Acta - Proteins and Proteomics, 1854 :1382-1391. [DOI] Link to full text [Details]
Cleary JA, Doherty W, Evans P, Malthouse JPG (2014) 'Hemiacetal stabilization in a chymotrypsin inhibitor complex and the reactivity of the hydroxyl group of the catalytic serine residue of chymotrypsin'. Biochimica et Biophysica Acta - Proteins and Proteomics, 1844 :1119-1127. [DOI] Link to full text [Details]
William Doherty, Jinju James, Paul Evans, Linda Martin, Nikoletta Adler, Derek Nolan and Andrew Knox (2014) 'Preparation, biological Evaluation and Localisation Studies of a Series of Dipeptide-based Vinyl Sulfones'. Organic and Biomolecular Chemistry, 12 :7561. [Details]
Noel McLaughlin, Paul Evans and Mark Pines (2014) 'The Chemistry and Biology of Febrifugine and Halofuginone'. Bioorganic and Medicinal Chemistry, 22 :1993. [Details]
Kimberly Geoghegan and Paul Evans (2014) 'Synthesis of (R)-Perillyl alcohol from (R)-Limonene'. Tetrahedron Letters, 55 :1431. [Details]
Dunny E, Doherty W, Evans P, Malthouse JP, Nolan D, Knox AJ (2013) 'Vinyl sulfone-based peptidomimetics as anti-trypanosomal agents: design, synthesis, biological and computational evaluation'. Journal of Medicinal Chemistry, 56 (17):6638-6650. [DOI] [Details]
K. Geoghegan, S. Smullen and P. Evans (2013) 'Halonium Ion Triggered Rearrangement of Unsaturated Benzo-Annulated Bi- and Tricyclic Sulfonamides'. Journal of Organic Chemistry, 78 :10443-10451. [Details]
Ortin, Y,Evans, P (2013) 'trans-Tetradec-2-enoic Acid in Impatiens glandulifera'. Synthetic Communications, 43 :1404-1412. [DOI] [Details]
Geoghegan, K,Evans, P (2013) 'Double Reduction of Cyclic Aromatic Sulfonamides: Synthesis of (+)-Mesembrine and (+)-Mesembranol'. Journal of Organic Chemistry, 78 :3410-3415. [Details]
Geoghegan, K,Evans, P,Rozas, I,Alkorta, I (2012) 'Regioselectivity in the Intramolecular Heck Reaction of a Series of Cyclic Sulfonamides: An Experimental and Computational Study'. Chemistry - A European Journal, 18 :13379-13387. [DOI] [Details]
O'Byrne, A,O'Reilly, S,Tighe, C,Evans, P,Ciuffini, L,Santoro, MG (2012) 'Temporary thio-derivatization in the synthesis of (+)-4-acetylbromoxone'. Tetrahedron Letters, 53 :5936-5938. [DOI] [Details]
Geoghegan, K,Kelleher, S,Evans, P; (2011) 'An Investigation into the One-Pot Heck Olefination-Hydrogenation Reaction'. Journal of Organic Chemistry, 76 :2187-2194. [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, Klein JE, Geoghegan K, Meral N, ; (2010) 'Selective generation of quaternary all-carbon-centres through Heck-cyclisations: synthesis of mesembrane'. Chemical Communications, 46 (6):937-939. [DOI] [Details]
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]
McLaughlin, NP,Butler, E,Evans, P,Brunton, NP,Koidis, A,Rai, DK; (2010) 'A short synthesis of (+) and (-)-falcarinol'. Tetrahedron, 66 :9681-9687. [DOI] [Details]
Dunny, E,Evans, P; (2010) 'Stereocontrolled Synthesis of the PPAR-gamma Agonist 10-Nitrolinoleic Acid'. Journal of Organic Chemistry, 75 :5334-5336. [DOI] [Details]
O'Byrne, A,Murray, C,Keegan, D,Palacio, C,Evans, P,Morgan, BS; (2010) 'The thio-adduct facilitated, enzymatic kinetic resolution of 4-hydroxycyclopentenone and 4-hydroxycyclohexenone'. Organic and Biomolecular Chemistry, 8 :539-545. [DOI] [Details]
Brusey, SA,Banide, EV,Dorrich, S,O'Donohue, P,Ortin, Y,Muller-Bunz, H,Long, C,Evans, P,McGlinchey, MJ; (2009) 'X-ray Crystallographic and NMR Spectroscopic Study of (eta(2)-Alkene)(mu-alkyne)pentacarbonyldicobalt Complexes: Arrested Pauson-Khand Reaction Intermediates'. Organometallics, 28 :6308-6319. [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]
Klein, JEMN,Muller-Bunz, H,Evans, P; (2009) 'Studies concerning the electrophilic amino-alkene cyclisation for the synthesis of bicyclic amines'. Organic and Biomolecular Chemistry, 7 :986-995. [DOI] [Details]
Evans, P,Kavanagh, Y,O'Brien, M; (2009) 'Stereocontrolled preparation of bicyclic alkaloid analogues: an approach towards the kinabalurine skeleton'. Tetrahedron, 65 :8259-8268. [DOI] [Details]
Kavanagh, Y,Chaney, CM,Muldoon, J,Evans, P; (2008) 'Iridium-Mediated Isomerization-Cyclization of Bicyclic Pauson-Khand Derived Allylic Alcohols'. Journal of Organic Chemistry, 73 :8601-8604. [DOI] [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]
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 :7187. [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]
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]
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]
O'Byrne, A,Evans, P; (2008) 'Rapid synthesis of the tetrahydroquinoline alkaloids: angustureine, cuspareine and galipinine'. Tetrahedron, 64 :8067-8072. [DOI] [Details]
Stefanko, MJ,Gun'ko, YK,Rai, DK,Evans, P; (2008) 'Synthesis of functionalised polyethylene glycol derivatives of naproxen for biomedical applications'. Tetrahedron, 64 :10132-10139. [DOI] [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 :183. [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 :4733. [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 :2907. [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 :1830. [Details]
Duffy PE, Quinn SM, Roche HM & Evans P. ; (2006) 'Synthesis of trans-Vaccenic Acid and 9-cis- 11-trans-Conjugated Linoleic Acid'. Tetrahedron, . [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]
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]
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 :276-280. [DOI] [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]
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, 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]
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]
                                                                                                                     

Research

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.