School of Chemistry

Search site

Steve Marsden

Head of the School of Chemistry
Professor of Organic Chemistry
Member of the Process Research and Development group

Contact details

Room: G26
Tel: +44 (0)113 3436425
Email: S.P.Marsden@leeds.ac.uk

Keywords

Asymmetric synthesis
Development of New Catalytic Methods
Bioactive Target Synthesis
Organosilicon Chemistry


Photograph of Steve Marsden

Research interests

The main focus of our work is in the development and application of new synthetic methods. Recent and ongoing projects include:

  1. Development of methods for the construction of diverse quaternary asymmetric centres. Avenues of exploration include (a) the chemistry of heteroatom-substituted extended enolates; (b) the first asymmetric variants of the aza-Wittig reaction; and (c) metal-catalysed asymmetric arylation protocols.
  2. Development of new efficient catalytic methods (both metal and organocatalysed) for fine chemical synthesis. Examples include new catalytic hydrogenation catalysis and catalytic approaches to the de novo assembly of heteroaromatics.
  3. Application of the above methods to target synthesis of bioactive natural products. Recent completed syntheses include the complex amino acid myriocin, tetrahydrofuran-containing compounds such as monocerin, virgatusin and the core of the eunicellins, and the indolizidine alkaloid tashiromine. Current targets include complex indole alkaloids such as the okaramines.
The work is supported by the EPSRC, Royal Society (Industry Fellowship 2008-10 to SPM), AstraZeneca, GlaxoSmithKline, NPIL Pharmaceuticals, Pfizer and Syngenta.

Useful links

Marsden research group   
   
   

Publications

Johnson TC, Marsden SP A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines Beilstein Journal of Organic Chemistry 12 1-4, 2016
DOI:10.3762/bjoc.12.1
View abstract

Watson EL, Ball A, Raw SA, Marsden SP Synthetic Studies on Psychotrimine: Palladium-Catalysed Arylation of 2-(N -Indolyl) Amides Synlett 27 146-150, 2016
DOI:10.1055/s-0035-1560519
View abstract

Colomer I, Empson CJ, Craven P, Owen Z, Doveston RG, Churcher I, Marsden SP, Nelson A A divergent synthetic approach to diverse molecular scaffolds: Assessment of lead-likeness using LLAMA, an open-access computational tool Chemical Communications 52 7209-7212, 2016
DOI:10.1039/c6cc03244c
View abstract

Foley DJ, Nelson A, Marsden SP Evaluating New Chemistry to Drive Molecular Discovery: Fit for Purpose? Angewandte Chemie - International Edition -, 2016
DOI:10.1002/anie.201604193
View abstract

Sambiagio C, Munday RH, John Blacker A, Marsden SP, McGowan PC Green alternative solvents for the copper-catalysed arylation of phenols and amides RSC Advances 6 70025-70032, 2016
DOI:10.1039/c6ra02265k
View abstract

Firth JD, Craven PGE, Lilburn M, Pahl A, Marsden SP, Nelson A A biosynthesis-inspired approach to over twenty diverse natural product-like scaffolds Chemical Communications 52 9837-9840, 2016
DOI:10.1039/c6cc04662b
View abstract

Leonard J, Blacker AJ, Marsden SP, Jones MF, Mulholland KR, Newton R A Survey of the Borrowing Hydrogen Approach to the Synthesis of some Pharmaceutically Relevant Intermediates Organic Process Research and Development 19 1400-1410, 2015
DOI:10.1021/acs.oprd.5b00199
View abstract

Craven P, Aimon A, Dow M, Fleury-Bregeot N, Guilleux R, Morgentin R, Roche D, Kalliokoski T, Foster R, Marsden SP, Nelson A Design, synthesis and decoration of molecular scaffolds for exploitation in the production of alkaloid-like libraries Bioorganic and Medicinal Chemistry 23 2629-2635, 2015
DOI:10.1016/j.bmc.2014.12.048
View abstract

Colomer I, Adeniji O, Burslem GM, Craven P, Rasmussen MO, Willaume A, Kalliokoski T, Foster R, Marsden SP, Nelson A Aminomethylhydroxylation of alkenes: Exploitation in the synthesis of scaffolds for small molecule libraries Bioorganic and Medicinal Chemistry 23 2736-2740, 2015
DOI:10.1016/j.bmc.2015.01.058
View abstract

Foley DJ, Doveston RG, Churcher I, Nelson A, Marsden SP A systematic approach to diverse, lead-like scaffolds fromα,α-disubstituted amino acids. Chemical Communications -, 2015
DOI:10.1039/c5cc03002a
View abstract

Firth JD, Zhang R, Morgentin R, Guilleux R, Kalliokoski T, Warriner S, Foster R, Marsden SP, Nelson A Exploitation of the Ugi-Joullié Reaction in the Synthesis of Libraries of Drug-Like Bicyclic Hydantoins Synthesis (Germany) 47 2391-2406, 2015
DOI:10.1055/s-0034-1378704
View abstract

Doveston RG, Tosatti P, Dow M, Foley DJ, Li HY, Campbell AJ, House D, Churcher I, Marsden SP, Nelson A A unified lead-oriented synthesis of over fifty molecular scaffolds Organic and Biomolecular Chemistry 13 859-865, 2015
DOI:10.1039/c4ob02287d
View abstract

Sambiagio C, Munday RH, Marsden SP, Blacker AJ, McGowan PC Picolinamides as effective ligands for copper-catalysed aryl ether formation: Structure-activity relationships, substrate scope and mechanistic investigations Chemistry - A European Journal 20 17606-17615, 2014
DOI:10.1002/chem.201404275
View abstract

Sambiagio C, Munday RH, Marsden SP, Blacker AJ, McGowan PC Picolinamides as effective ligands for copper-catalysed aryl ether formation: structure-activity relationships, substrate scope and mechanistic investigations Chemistry (Weinheim an der Bergstrasse, Germany) 20 17606-17615, 2014
DOI:10.1002/chem.201404275
View abstract

Webb NJ, Marsden SP, Raw SA Rhodium(III)-Catalyzed C-H Activation/Annulation with Vinyl Esters as an Acetylene Equivalent Organic Letters 16 4718-4721, 2014
DOI:10.1021/ol502095z
View abstract

Li HY, Horn J, Campbell A, House D, Nelson A, Marsden SP A convergent rhodium-catalysed asymmetric synthesis of tetrahydroquinolines. Chem Commun (Camb) 50 10222-10224, 2014
DOI:10.1039/c4cc04940c
View abstract

Lanaro R, Frodsham L, Marsden SP Hydrogen borrowing methodology: New iridium(III) catalysts for amine alkylation reactions, 2014

Webb NJ, Marsden SP, Raw SA Vinyl esters as acetylene synthons: Rhodium(III)-catalysed C-H activation for the synthesis of isoquinolones and isoquinolines, 2014

Foley DJ, Nelson AS, Marsden SP Realising lead-oriented synthesis (LOS): A powerful approach to diverse, lead-like, small molecule scaffolds, 2014

Crossley JA, Marsden SP, Clemens I Exploring azide alternatives: Novel applications of the catalytic aza-Wittig reaction, 2014

Sambiagio C, Marsden SP, Blacker AJ, McGowan PC Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development. Chem Soc Rev 43 3525-3550, 2014
DOI:10.1039/c3cs60289c
View abstract

Zhao Y, Blacker J, Marsden S Sustainable aromatics: Synthesis and hydrogenolysis of trisubstituted-1,3,5-triazines with lignin monomer compounds, 2014

Marsden SP Catalytic Variants of Phosphine Oxide-Mediated Organic Transformations In Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries , 2013
DOI:10.1002/9781118354520.ch15

Winkworth PGA, Blacker J, Marsden SP, Telford A, Ford GJG Catalytic hydrogen transfer in polycyclic indole formation, 2013

Tosatti P, Nelson A, Marsden SP Recent advances and applications of iridium-catalysed asymmetric allylic substitution. Org Biomol Chem 10 3147-3163, 2012
DOI:10.1039/c2ob07086c
View abstract

Li HY, Horn J, Shearer RJ, Marsden SP, Nelson A, Campbell AJ, House D, Weingarten GG Rhodium-catalyzed conjugate addition with functionized boronate: Divergent access to various building blocks with lead-like molecular properties, 2012

Tosatti P, Campbell AJ, House D, Nelson A, Marsden SP Catalyst control in sequential asymmetric allylic substitution: stereodivergent access to N,N-diprotected unnatural amino acids. J Org Chem 76 5495-5501, 2011
DOI:10.1021/jo200720c
View abstract

Tosatti P, Campbell AJ, House D, Nelson A, Marsden SP Iridium-catalyzed asymmetric allylic amination with polar amines: Access to building blocks with lead-like molecular properties, 2011

Tosatti P, Campbell AJ, House D, Nelson A, Marsden SP Catalyst control in sequential asymmetric allylic substitution: Stereodivergent access to N,N-diprotected unnatural amino acids, 2011

Tosatti P, Horn J, Campbell AJ, House D, Nelson A, Marsden SP Iridium-Catalyzed Asymmetric Allylic Amination with Polar Amines: Access to Building Blocks with Lead-Like Molecular Properties ADV SYNTH CATAL 352 3153-3157, 2010
DOI:10.1002/adsc.201000721

Saidi O, Bamford MJ, Blacker AJ, Lynch J, Marsden SP, Plucinski P, Watson RJ, Williams JMJ Iridium-catalyzed formylation of amines with paraformaldehyde TETRAHEDRON LETT 51 5804-5806, 2010
DOI:10.1016/j.tetlet.2010.08.106

Saidi O, Bamford MJ, Blacker AJ, Lynch J, Marsden SP, Plucinski P, Watson RJ, Williams JMJ Iridium-catalyzed formylation of amines with paraformaldehyde TETRAHEDRON LETTERS 51 5804-5806, 2010
DOI:10.1016/j.tetlet.2010.08.106

Glowacki DR, Liang CH, Marsden SP, Harvey JN, Pilling MJ Alkene hydroboration: hot intermediates that react while they are cooling. J Am Chem Soc 132 13621-13623, 2010
DOI:10.1021/ja105100f
View abstract

Saidi O, Blacker AJ, Lamb GW, Marsden SP, Taylor JE, Williams JMJ Borrowing Hydrogen in Water and Ionic Liquids: Iridium-Catalyzed Alkylation of Amines with Alcohols ORG PROCESS RES DEV 14 1046-1049, 2010
DOI:10.1021/op100024j

Saidi O, Blacker AJ, Farah MM, Marsden SP, Williams JMJ Iridium-catalysed amine alkylation with alcohols in water CHEM COMMUN 46 1541-1543, 2010
DOI:10.1039/b923083a

Marsden SP ORGANIC SYNTHESIS The Wittig reaction cleans up NAT CHEM 1 685-687, 2009
DOI:10.1038/nchem.458

Blacker AJ, Farah MM, Marsden SP, Saidi O, Williams JMJ Oxidative conversion of amines into benzoxazoles using hydrogen transfer catalysis TETRAHEDRON LETT 50 6106-6109, 2009
DOI:10.1016/j.tetlet.2009.08.042

Horn J, Li HY, Marsden SP, Nelson A, Shearer RJ, Campbell AJ, House D, Weingarten GG Convergent synthesis of dihydroquinolones from o-aminoarylboronates TETRAHEDRON 65 9002-9007, 2009
DOI:10.1016/j.tet.2009.06.103

Glowacki DR, Marsden SP, Pilling MJ Significance of nonstatistical dynamics in organic reaction mechanisms: time-dependent stereoselectivity in cyclopentyne-alkene cycloadditions. J Am Chem Soc 131 13896-13897, 2009
DOI:10.1021/ja9043054
View abstract

Marsden SP, Steer JT, Orlek BS Synthesis ofα-silylalkylbenzoxazoles and oxazoles from stable silylketenes Tetrahedron 65 5503-5512, 2009
DOI:10.1016/j.tet.2009.03.105
View abstract

Watson EL, Marsden SP, Raw SA A robust, efficient catalyst system for enolate arylation leading to quaternary 3-aminooxindoles TETRAHEDRON LETT 50 3318-3320, 2009
DOI:10.1016/j.tetlet.2009.02.076

Blacker AJ, Farah MM, Hall MI, Marsden SP, Saidi O, Williams JM Synthesis of benzazoles by hydrogen-transfer catalysis. Org Lett 11 2039-2042, 2009
DOI:10.1021/ol900557u
View abstract

McElhinney AD, Marsden SP STEREOSELECTIVE SYNTHESIS OF 2,3,5-TRISUBSTITUTED PYRROLIDINES USING METATHESIS-DERIVED beta-AMINOALLYLSILANES HETEROCYCLES 79 417-422, 2009
DOI:10.3987/COM-08-S(D)55

Tosatti P, Marsden SP, Nelson AS, House D, Weingarten GG ORGN 431-Iterative cross-metathesis and Cu-catalyzed asymmetric allylic substitution: Matched and mismatched effects ABSTR PAP AM CHEM S 237 -, 2009

Saidi O, Blacker AJ, Farah MM, Marsden SP, Williams JMJ Selective Amine Cross-Coupling Using Iridium-Catalyzed "Borrowing Hydrogen" Methodology ANGEW CHEM INT EDIT 48 7375-7378, 2009
DOI:10.1002/anie.200904028

Horn J, Marsden SP, Nelson A, House D, Weingarten GG Convergent, regiospecific synthesis of quinolines from o-aminophenylboronates ORG LETT 10 4117-4120, 2008
DOI:10.1021/ol8016726

Jones MC, Marsden SP Total synthesis of the immunosuppressants myriocin and 2-epi-myriocin ORG LETT 10 4125-4128, 2008
DOI:10.1021/ol801709c

Jia YX, Hillgren JM, Watson EL, Marsden SP, Kundig EP Chiral N-heterocyclic carbene ligands for asymmetric catalytic oxindole synthesis CHEM COMMUN 4040-4042, 2008
DOI:10.1039/b810858g

Marsden SP, Raw S, Watson EL ORGN 161-General synthesis of quaternary 3-aminooxindoles by palladium catalyzed enolate arylation, 2008

Hillgren JM, Marsden SP Convenient synthesis of 3-alkoxy-3-aryloxindoles by intramolecular arylation of mandelic amides. J Org Chem 73 6459-6461, 2008
DOI:10.1021/jo8010842
View abstract

Marsden SP, Watson EL, Raw SA Facile and general synthesis of quaternary 3-aminooxindoles ORG LETT 10 2905-2908, 2008
DOI:10.1021/ol801028e

Marsden SP, McGonagle AE, McKeever-Abbas B Catalytic aza-Wittig cyclizations for heteroaromatic synthesis. Org Lett 10 2589-2591, 2008
DOI:10.1021/ol800921n
View abstract

Marsden SP, McElhinney AD Total synthesis of the indolizidine alkaloid tashiromine. Beilstein J Org Chem 4 8-, 2008
DOI:10.1186/1860-5397-4-8
View abstract

Jackman H, Marsden SP, Shapland P, Barrett SA Isotopic Labelling for Determination of Enantiomeric Purity by 2H NMR Spectroscopy Organic Letters 9 5179-5182, 2007

Marsden SP, Newton R Electrophile-Directed Diastereoselective Alkylation of Prochiral Enediolates Journal of the American Chemical Society 129 12600-12601, 2007
DOI:10.1021/ja073624e

Headley CE, Marsden SP Synthesis and application of P-stereogenic phosphines as superior reagents in the asymmetric aza-Wittig reaction. J Org Chem 72 7185-7189, 2007
DOI:10.1021/jo0709908
View abstract

Akindele T, Marsden SP, Cumming JG, Yamada K, Tomioka K AEI 79-Stereoselective synthesis of 2,3,4,5 tetrasubstituted tetrahydrofurans: Application to the total synthesis of (+)-Virgatusin and b) asymmetric radical additions to chiral sulfinimines ABSTR PAP AM CHEM S 234 -, 2007

Marsden SP Contemporary organosilicon chemistry Beilstein Journal of Organic Chemistry 3 -, 2007

Jones M, Marsden SP, Subtil M Efficient asymmetric synthesis of quaternary (E)-vinylglycines by deconjugative alkylation of dehydroamino acids Organic Letters 8 5509-5512, 2006
DOI:10.1021/ol062162r

Marsden SP, Newton R ORGN 952-Electrophile-controlled diastereoselective alkylation of dienediolates: Towards cinatrin B ABSTR PAP AM CHEM S 232 -, 2006

Lertpibulpanya D, Marsden SP, Rodriguez-Garcia I, Kilner CA Asymmetric Aza-Wittig Reactions: Enantioselective Synthesis ofâ-Quaternary Azacycles Angewandte Chemie - International Edition 45 5000-5002, 2006
DOI:10.1002/anie.200601383

Blakemore P, Marsden SP, Vater H Reagent-controlled asymmetric homologation of boronic esters by enantioenriched main-group chiral carbenoids Organic Letters 8 773-776, 2006
DOI:10.1021/ol053055k

Lertpibulpanya D, Marsden SP Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones Organic&Biomolecular Chemistry 4 3498-3504, 2006
DOI:10.1039/b608801e

Cassidy JH, Farthing CN, Marsden SP, Pedersen A, Slater MJ, Stemp G A concise, convergent total synthesis of monocerin Organic&Biomolecular Chemistry 4 4118-4126, 2006

Alexander PA, Marsden SP, Muñoz Subtil DM, Reader JC Deconjugation of dehydroamino acids: stereoselective synthesis of racemic (E)-vinylglycines. Org Lett 7 5433-5436, 2005
DOI:10.1021/ol052139q
View abstract

Newton R, Marsden SP Efficient Synthesis of Quaternaryα-Hydroxy Acids by Alkylation ofα-Ketoamide-Derived Dienediolates Synthesis 19 3263-3270, 2005
DOI:10.1055/s-2005-918481

McElhinney AD, Marsden SP A concise synthesis of tashiromine SYNLETT 2528-2530, 2005
DOI:10.1055/s-2005-917072

Marsden SP, Ducept PC Synthesis of highly substituted allenylsilanes by alkylidenation of silylketenes BEILSTEIN J ORG CHEM 1 -, 2005
DOI:10.1186/1860-5397-1-5

Akindele T, Marsden SP, Cumming JG Stereocontrolled Assembly of Tetrasubstituted Tetrahydrofurans: A Concise Synthesis of Virgatusin Organic Letters 7 3685-3688, 2005
DOI:10.1021/ol051292h

Marsden SP, Akindele T, Cumming JG Stereoselective Synthesis of the octahydroisobenzofuran skeleton of the eunicellins Tetrahedron Letters 46 7235-7238, 2005
DOI:10.1016/j.tetlet.2005.08.046

Marsden SP Product class 9: enones In Science of synthesis , 2005

Miles SM, Marsden SP, Leatherbarrow RJ, Coates WJ Reagent-Controlled Stereoselective Synthesis of Lignan-Related Tetrahydrofurans The Journal of Organic Chemistry (Washington) 69 6874-6882, 2004
DOI:10.1021/jo048971a

Miles SM, Marsden SP, Leatherbarrow RJ, Coates WJ A novel, stereoselective and convergent synthesis of aryltetralins Chemical Communications 20 2292-2293, 2004
DOI:10.1039/b409528f

Miles SM, Leatherbarrow RJ, Marsden SP, Coates WJ Synthesis and bio-assay of RCM-derived Bowman-Birk inhibitor analogues Organic&Biomolecular Chemistry 2 281-283, 2004
DOI:10.1039/b312908j

Marsden SP, Jamal J, Fray MJ Desymmetrising aza-Wittig reactions., 2003

Marsden SP, Alexander P, Reader JC Practical routes for the synthesis of beta,gamma-unsaturated amino acids., 2003

Marsden SP, Jamal J, Fray JM Desymmetrising aza-wittig reactions. Abstracts of Papers of the American Chemical Society 226 pp.122-, 2003

Marsden SP, Alexander P, Reader JC Practical routes for the synthesis of beta,gamma-unsaturated amino acids. Abstracts of Papers of the American Chemical Society 226 pp.142-, 2003

Marsden SP, Subtil DMM Concise asymmetric approaches to myriocin. ABSTR PAP AM CHEM S 224 U170-U170, 2002

Marsden SP, Subtil M, Dulce M Concise asymmetric approaches to myriocin, 2002

Marsden SP, Ducept PD Inter- and intramolecular Diels-Alder/retro-Diels-Alder reactions of 4-silylated oxazoles Arkivoc (Archive for Organic Chemistry) 22-34, 2002