Dr David Lupton - Researcher Profile

David Lupton

Address

School of Chemistry
Building 19, Clayton

Biography

Fundamental science opens door to future applications

Dr David Lupton likens catalysis to a modern-day Philosopher’s Stone. Many believed this mythical substance could turn base metals into gold, and David thinks that by converting cheap chemicals into valuable materials for society, catalysis is achieving a modern day equivalent. He hopes that by focusing on fundamental research, such as this transformative process, he can create a foundation for new applications in the future.

Catalysis of chemical reactions involves accelerating the rate of a reaction with an additive that is itself not consumed.

“I’m able to take commodity-cheap chemicals and convert them into valuable chemicals, using something that isn’t consumed in the process,” David explains. “That is an efficient and powerful way of generating valuable materials. My research focuses on the discovery of new catalysts and catalytic reactions that allow us to make the chemicals that can see applications in a range of associated disciplines.”

“If you can make something valuable from something cheap, and not consume the thing that allows that to occur, it’s a highly sustainable procedure,” David says.

David says many important scientific discoveries have only been possible through a fundamental understanding of reactivity. But he thinks we still know very little about it.

“My drive for why I do science is about enabling discovery,” David says. “We discover new catalytic reactivity to allow scientists to access materials that they’ve never had before. We have some projects that have more obvious application and others that are really just about saying ‘I can teach people how to make something that’s never been made before’. Then it’s for their imagination to run with and see if they can put it in a device.”

Total synthesis is another aspect of David’s focus on fundamental science. This involves the complete chemical synthesis of organic molecules from simpler, commercially-available pieces.

“There are lots of interesting medicinal entities in nature,” David admits, but adds the question: “can we design more efficient ways of manufacturing them in a chemical lab that allow you to use cheaper, more readily available materials?”

David is also collaborating with the CSIRO to develop iridoid-based natural products that could lead to future applications in medicinal chemistry.

“We have technology that allows us to access these types of materials very quickly,” David says. “We’ve been able to build families of these molecules that you can’t access easily using other techniques. Our technology allows us to get to these families so we can start looking at their biology profiles, to see if there is biological activity.”

But, overall, David believes we’re doing ourselves a disservice if we ignore the importance of fundamental science.

“Applied science builds on, amongst other things, new discoveries in chemical reactivity. My perspective is ‘we’ve discovered new reactivity, how can that be used?’ The applications can be in a medicinal context. I’m not averse to that, but the legacy that is potentially more interesting to me is perhaps in 50 or 100 years, when a scientist does something that they wouldn’t have been able to do without knowledge that we have gained today.”

Keywords

catalysis, total synthesis

Qualifications

DOCTOR OF PHILOSOPHY
Institution: ANU -Canberra
Year awarded: 2005
BACHELOR OF SCIENCE (HONOURS)
Institution: The Uni of Adelaide
Year awarded: 2000

Publications

Journal Articles

Pandiancherri, S., Ryan, S.J., Lupton, D., 2012, 1,3-dipolar cycloaddition of unstabilised azomethine ylides by lewis base catalysis, Organic & Biomolecular Chemistry [P], vol 10, issue 39, Royal Society of Chemistry, United Kingdom, pp. 7903-7911.

Candish, L., Lupton, D., 2012, N-heterocyclic carbene cascade catalysis: Dual Bronsted/Lewis base rearrangement of cyclopropyl enol esters to dihydropyranones, Chemical Science [P], vol 3, issue 2, Royal Society of Chemistry, Cambridge England, pp. 380-383.

Hierold, J., Lupton, D., 2012, Synthesis of spirocyclic gamma-lactones by cascade beckwith-dowd ring expansion/cyclization, Organic Letters [P], vol 14, issue 13, American Chemical Society, Washington DC United States, pp. 3412-3415.

Ryan, S.J., Stasch, A., Paddon-Row, M.N., Lupton, D., 2012, Synthetic and quantum mechanical studies into the N-heterocyclic carbene catalyzed (4+2) cycloaddition, Journal Of Organic Chemistry [P], vol 77, issue 2, American Chemical Society, Washington DC United States, pp. 1113-1124.

Gass, I., Gartshore, C., Lupton, D., Moubaraki, B., Nafady, A., Bond, A., Boas, J., Cashion, J., Milsmann, C., Wieghardt, K., Murray, K., 2011, Anion dependent redox changes in iron bis-terdentate nitroxide {NNO} chelates, Inorganic Chemistry [P], vol 50, issue 7, American Chemical Society, Washington Detroit USA, pp. 3052-3064.

Gee, W., Hierold, J., MacLellan, J., Andrews, P., Lupton, D., Junk, P., 2011, Chiral lanthanoid dimers ligated by carbohydrate-based diketonates: Catalytic and luminescent properties, European Journal of Inorganic Chemistry [P], vol 2011, issue 25, Wiley-Blackwell, Malden Massachusetts USA, pp. 3755-3760.

Candish, L., Lupton, D., 2011, Concise formal synthesis of (-)-7-deoxyloganin via n-heterocyclic carbene catalysed rearrangement of alpha,beta-unsaturated enol esters, Organic & Biomolecular Chemistry [P], vol 9, issue 23, Royal Society of Chemistry, Cambridge UK, pp. 8182-8189.

Ryan, S., Candish, L., Martinez, I., Lupton, D., 2011, Enabling the development of N-heterocyclic carbene (NHC) catalyzed reactions: practical methods for the preparation of 1-acyl-2-alkylcycloalkenes from cycloalkanones, Australian Journal of Chemistry [E], vol 64, issue 8, CSIRO Publishing, Collingwood Vic Australia, pp. 1148-1157.

Ngatimin, M., Frey, R., Andrews, C., Lupton, D., Hutt, O., 2011, Iodobenzene catalysed synthesis of spirofurans and benzopyrans by oxidative cyclisation of vinylogous esters, Chemical Communications [P], vol 47, issue 42, Royal Society of Chemistry, United Kingdom, pp. 11778-11780.

Ryan, S., Candish, L., Lupton, D., 2011, N-heterocyclic carbene (NHC)-catalyzed all-carbon [4+2] cycloaddition-decarboxylation, Synlett [P], vol 16, Georg Thieme Verlag KG, Germany, pp. 2275-2278.

Ryan, S., Candish, L., Lupton, D., 2011, N-heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with alpha,beta-unsaturated acid fluorides, Journal Of The American Chemical Society [P], vol 133, issue 13, American Chemical Society, USA, pp. 4694-4697.

Banwell, M.G., Jones, M.T., Loong, D.T.J., Lupton, D.W., Pinkerton, D.M., Ray, J.K., Willis, A.C., 2010, A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclization approach to C-3 mono-alkylated oxindoles and related compounds, Tetrahedron [P], vol 66, issue 47, Pergamon Elsevier Science Ltd, Oxford England, pp. 9252-9262.

Hierold, J., Gray-Weale, A., Lupton, D., 2010, A divergent synthesis of modular dendrimers via sequential C-C bond fragmentation thio-michael addition, Chemical Communications [E], vol 46, issue 36, Royal Society of Chemistry, UK, pp. 6789-6791.

Pandiancherri, S., Lupton, D.W., 2010, Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation, Tetrahedron Letters [P], vol 52, issue 6, Pergamon-Elsevier Science Ltd, England, pp. 671-674.

Gartshore, C., Lupton, D., 2010, Readily accessible oxazolidine nitroxyl radicals: bifunctional cocatalysts for simplified copper based aerobic oxidation, Advanced Synthesis and Catalysis [P], vol 352, issue 18, Wiley-VCH Verlag GmbH, Weinheim Germany, pp. 3321-3328.

Hierold, J., Hsia, T., Lupton, D.W., 2010, The Grob/Eschenmoser fragmentation of cycloalkanones bearing beta-electron withdrawing groups: a general strategy to acyclic synthetic intermediates, Organic & Biomolecular Chemistry [P], vol 9, issue 3, Royal Society of Chemistry, Cambridge England, pp. 783-792.

Ngatimin, M., Lupton, D., 2010, The discovery of catalytic enantioselective polyvalent iodine mediated reactions, Australian Journal of Chemistry [E], vol 63, issue 4, CSIRO Publishing, Collingwood Vic Australia, pp. 653-658.

Candish, L., Lupton, D.W., 2010, The total synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalyzed rearrangement of alpha,beta-unsaturated enol esters, Organic Letters [P], vol 12, issue 21, American Chemical Society, Washington DC USA, pp. 4836-4839.

Ryan, S.J., Thompson, C.D., Lupton, D.W., 2009, A synthetic and computational investigation into the direct synthesis of alpha-hydroxymethylated enones from beta-keto phosphonates, Australian Journal of Chemistry [E], vol 62, issue 7, CSIRO, Melbourne, Australia, pp. 720-727.

Ryan, S.J., Candish, L., Lupton, D.W., 2009, N-heterocyclic carbene-catalyzed generation of alpha,beta-unsaturated acyl imidazoliums: Synthesis of dihydropyranones by their reaction with enolates, Journal Of The American Chemical Society [P], vol 131, issue 40, American Chemical Society, USA, pp. 14176-14177.

Ngatimin, M., Gartshore, C.J., Kindler, J.P., Naidu, S., Lupton, D.W., 2009, The alpha-halogenation of alpha,beta-unsaturated carbonyls and dihalogenation of alkenes using bisacetoxyiodobenzene/pyridine hydrohalides, Tetrahedron Letters [P], vol 50, issue 44, Elsevier, The Netherlands, pp. 6008-6011.

Harvey, M.J., Banwell, M., Lupton, D., 2008, The synthesis of compounds related to the indole-indoline core of the vinca alkaloids (+)-vinblastine and (+)-vincristine, Tetrahedron Letters [P], vol 49, issue 32, Elsevier, Netherlands, pp. 4780-4783.

Lupton, D., Trost, B.M., 2007, Dinuclear zinc-catalyzed enantioselective aza-henry reaction, Organic Letters, vol 9, American Chemical Society, USA, pp. 2023-2026.

Banwell, M., Lupton, D., 2006, Tandem radical cyclization reactions, initiated at nitrogen, as an approach to the CDE-tricylic cores of certain post-secodine alkaloids, Heterocycles, vol 68, Japan Institute of Heterocyclic Chemistry, Japan, pp. 71-92.

Banwell, M., Lupton, D., Willis, A., 2005, Application of the palladium(0)-catalyzed ullmann cross-coupling reaction in a total synthesis of (plusminus)-aspidospermidine and thus representing an approach to the lower hemisphere of the binary indole-indoline alkaloid vinblastine, Australian Journal of Chemistry, vol 58, CSIRO, Australia, pp. 722-737.

Banwell, M., Lupton, D., 2005, Exploiting the palladium[0]-catalysed Ullmann cross-coupling reaction in natural products chemistry: Application to a total synthesis of the alkaloid (plus or minus)-aspidospermidine, Organic biomolecular chemistry, vol 3, Royal Society of Chemistry, UK, pp. 213-215.

Banwell, M., Edwards, A.J., Lupton, D., Whited, G., 2005, Whole-cell biotransformation of m-ethyltoluene into 1S,6R-5-ethyl-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic acid as an approach to the C-ring of the binary indole-indoline alkaloid vinblastine, Australian Journal of Chemistry, vol 58, CSIRO, Australia, pp. 14-17.

Banwell, M., Lupton, D., Ma, X., Renner, J., Sydnes, M., 2004, Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with beta-halo-enals, -enones, or -esters, Organic Letters, vol 6, American Chemical Society, USA, pp. 2741-2744.

Banwell, M., Lupton, D., Kelly, B., Kokas, o.J., 2003, Synthesis of Indoles via Palladium[0]-Mediated Ullmann Cross-Coupling of o-Halonitroarenes with Alpha-Halo-enones or -enals, Organic Letters, vol 5, American Chemical Society, USA, pp. 2497-2500.

Avery, T.D., Jenkins, N.F., Kimber, M.C., Lupton, D., Taylor, D.K., 2002, First Examples of the Catalytic Asymmetric Ring-opening of meso-1,2-Dioxines Utilising Cobalt(II) Complexes with Optically Active Tetradentate Schiff Base Ligands: Formation of Enantioenriched Cyclopropanes, Chemical Communications, vol 1, Royal Society Chemistry, UK, pp. 28-29.

Lupton, D., Taylor, D.K., 2002, New Mechanistic Aspects on the Catalytic Transformation of Vinylthiiranes to Mono and Disubsittuted 3,6-Dihydro-1,2-Dithiins by Tugsten Pentacarbonyl Monoacetonitrile, Tetrahedron, vol 58, Pergamon-Elsevier Science Ltd, UK, pp. 4517-4527.

Postgraduate Research Supervisions

Current Supervision

Program of Study:
(DOCTORATE BY RESEARCH).
Thesis Title:
Chemical synthesis- Green Catalysis.
Supervisors:
Lupton, D (Main), Thompson, C (Associate).
Program of Study:
(DOCTORATE BY RESEARCH).
Thesis Title:
Enantioselective Hypervalent I(III) - Mediated C-C and C-X Bond Forming Reactions..
Supervisors:
Lupton, D (Main).
Program of Study:
(DOCTORATE BY RESEARCH).
Thesis Title:
Intercepting the Coates Claisen and Ireland-Coates Claisen rearrangements.
Supervisors:
Lupton, D (Main), Wilkinson, B (Associate).
Program of Study:
(DOCTORATE BY RESEARCH).
Thesis Title:
New aspects of palladium catalysis using chiral phosphines and their application to the total synthesis of aspidophytidine and related natural products..
Supervisors:
Lupton, D (Main), Wilkinson, B (Associate).
Program of Study:
(DOCTORATE BY RESEARCH).
Thesis Title:
New reactions with alpha, beta unsaturated acyl azoliums catalyzed by N-heterocyclic carbenes as org.
Supervisors:
Lupton, D (Main), Murray, K (Associate).
Program of Study:
(DOCTORATE BY RESEARCH).
Thesis Title:
Organocatalysis using N-Heterocyclic Carbenes: The total synthesis of (-)-7-deoxyloganin and investigation into the homo Michael reaction..
Supervisors:
Lupton, D (Main).
Program of Study:
(DOCTORATE BY RESEARCH).
Thesis Title:
Studies into an NHC catalysed enantioselctive claisen rearrangement.
Supervisors:
Lupton, D (Main), Bell, T (Associate).
Program of Study:
(DOCTORATE BY RESEARCH).
Thesis Title:
The development of N-chloraamines as intermediates in organic synthesis: application towards the synthesis of indole alkaloids.
Supervisors:
Lupton, D (Main), Stasch, A (Associate).

Completed Supervision

Student:
Hierold, J.
Program of Study:
Exploration of haloalkylated beta-ketoesters in C-C bond fragmentation and radical cascade reactions. (PHD) 2012.
Supervisors:
Lupton, D (Main).
Student:
Ryan, S.
Program of Study:
N-heterocyclic carbenes as catalysts for substrates in the ester oxidation state. (PHD) 2012.
Supervisors:
Lupton, D (Main).