Current research can be broadly categorised under three main themes:
Approximately one third of today's best selling drugs are either natural products or have been developed based on lead structures provided by nature. Current research seeks to synthesize a number of natural products and reactive pharmacophores through the development of new chemical reactions based around organcatalysis.
In the field of organocatalysis, the amino acid proline finds almost unrivalled and ubiquitous use. Current work seeks to utilise this organocatalyst to assemble precursors for the total synthesis of natural products. A number of targets have already been successfull synthesized by undergraduate students at MacEwan.
Medicinal Chemistry (with ChemRoutes Corporation)
In the area of medicinal chemistry, a collaboration with ChemRoutes seeks to design and develop high throughput chemical libraries using parallel synthesis. These chemical libraries are being designed with new cancer and maleria therapeutics as the end goal.
ChemRoutes Corporation is a private drug discovery technology provider operating at the interface of organic chemistry, chemical biology, drug discovery and nanotechnology. It was established in 1999 and is headquartered in Edmonton. ChemRoutes Corporation has, as part of its mission, to make drug discovery affordable for its client base in the pharmaceutical, agrochemical and biotechnology industries.
There is a growing public concern for the presence of antibiotics and hormones in water and soil, and the possible pathway by which they enter the food chain. The concern focuses on the common use of these substances in agriculture. During their lifespan, roughly 60-80% of commercial livestock are treated with antibiotics and hormones, which serve as therapeutic, prophylactic or growth promoting agents, and much of the ingested dose is excreted unchanged or as active metabolites. Continuing effort has been made to enact the regulations to reduce and possibly prohibit the use of antibiotics and hormones as growth promoters. Concern over the potential negative health and ecological impacts of biologically active pharmaceuticals prompts the need for laboratory scale assessments.
This multi-faceted applied research project seeks to develop a practical approach for the detection, tracing and destruction of antibiotics and hormones in biowaste. This will enable further utilization of biowaste in production of sustainable and renewable energy, biofuels and other value-added products, and will provide regulatory agents with information to install adequate regulation policy.
The chemistry department at MacEwan has state of the art instrumentation, housed both within the chemistry teaching laboratories and in the dedicated instrument laboratory. The department has the following key capabilities, of particular importance to organic chemistry:
Opportunities exist for student involvement in this research. Student stipends are made available by Grant MacEwan University, the Alberta Association of Colleges and Technical Institutes, the Natural Sciences and Engineering Research Council, and private sector industries. If you are interested in working on these projects, please do not hesitate to get in touch.
Current and Former Research Students
9. Enantioselective synthesis of (R)-(-)-complanine, Krystal A. D. Kamanos, Jonathan M. Withey, Org. Biomol. Chem., 2012, 8, 1695-1699.
8. Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D, Jeremy Robertson, Praful T. Chovatia, Thomas G. Fowler, Jonathan M. Withey, Daniel J. Woollaston, Beilstein J. Org. Chem., 2010, 226-233.
7. Kinetic resolution and parallel kinetic resolution of methyl (±)-5-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis of 5-alkyl-cispentacin derivatives, Stephen G. Davies, A. Christopher Garner, Marcus J. C. Long, Rachel M. Morrison, Paul M. Roberts, Edward D. Savory, Andrew D. Smith, Miles J. Sweet and Jonathan M. Withey, Org. Biomol. Chem., 2005, 2762-2775.
6. Parallel kinetic resolution of tert-butyl (RS)-3-alkyl cyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkyl cispentacin derivatives, Stephen G. Davies, A. Christopher Garner, Marcus J. C. Long, Andrew D. Smith, Miles J. Sweet and Jonathan M. Withey, Org. Biomol. Chem., 2004, 3355-3362.
5. Kinetic resolution of tert-butyl (RS)-3-alkylcyclopentene-1-carboxylates for the synthesis of homochiral 3-alkyl-cispentacin and 3-alkyl-transpentacin derivatives, Mark E. Bunnage, Stephen G. Davies, Richard M. Parkin, Paul M. Roberts, Andrew D. Smith and Jonathan M. Withey, Org. Biomol. Chem., 2004, 3337-3354.
4. Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid, Mark E. Bunnage, Stephen G. Davies, Paul M. Roberts, Andrew D. Smith and Jonathan M. Withey, Org. Biomol. Chem., 2004, 2763-2776.
3. Asymmetric synthesis of (1R,2S,3R)-3-methylcispentacin and (1S,2S,3R)-3-methyltranspentacin by kinetic resolution of tert-butyl (RS)-3-methylcyclopentene-1-carboxylate, Mark E. Bunnage, Ann M. Chippindale, Stephen G. Davies, Richard M. Parkin, Andrew D. Smith and Jonathan M. Withey, Org. Biomol. Chem., 2003, 3698-3707.
2. Preparation of methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tert-butyl-cyclopentane-1-carboxylates by parallel kinetic resolution of methyl (RS)-5-tert-butyl-cyclopentene-1-carboxylate, Stephen G. Davies, David Diez, Mohamed M. El Hammouni, A. Christopher Garner, Narciso M. Garrido, Marcus J. C. Long, Rachel M. Morrison, Andrew D. Smith, Miles J. Sweet andJonathan M. Withey, Chem. Commun., 2003, 2410-2411.
1. Asymmetric synthesis of (1R,2S,3R)-gamma-methyl-cis-pentacin by a kinetic resolution protocol, Simon Bailey, Stephen G. Davies, Andrew D. Smith and Jonathan M. Withey, Chem. Commun., 2002, 2910-2911.