Dr Ben Greatrex

Senior Lecturer in Pharmacy - School of Science and Technology

Ben Greatrex

Phone: +61 02 6773 2402

Email: ben.greatrex@une.edu.au

Biography

I obtained my PhD from The University of Adelaide in 2004 working with Professor Dennis Taylor on the chemistry of organic peroxides and reactions that can be driven by the high energy peroxide bond. I then travelled to Wellington, NZ where I was employed for 3.5 years in the carbohydrate research group of Professor Richard Furneaux working on commercial drug discovery and competitive grant funded projects. These projects included the synthesis of glycodendrimers and saponins as vaccine adjuvants and the synthesis of some purine analogues. I then spent several years at the University of Wollongong with Professor Stephen Pyne on a Johnson and Johnson project using natural products as privileged scaffolds for drug discovery before joining UNE in 2010.

Qualifications

BSc (Hons), PhD (Chemistry) University of Adelaide

Memberships

Member of the Royal Australian Chemical Institute.

Consultancy Interests

Organic synthesis, contract synthesis and NMR spectroscopy

Teaching Areas

Teaching is an important part of academic work and I thoroughly enjoy seeing students develop into professional scientists and pharmacists. As a teacher, I take into account different abilities and learning styles through the use of an array of materials that are relevant to the student. Due to my background in drug development, much of my undergraduate teaching is at the interface of biology and chemistry. I have developed the units Pharmaceutical Science I and II at 1st and 2nd year level and I also teach medicinal, organic and analytical chemistry units.

Research Interests

My research is in the field of organic synthetic methodology, in particular the development of carbohydrates as precursors for the preparation of industrially relevant chemicals such as pharmaceutical starting materials, chiral auxiliaries and metal ligands. A recent focus has been on the production and use of the sugar pyrolysis product levoglucosenone as a biorenewable chemical and the development of new reaction processes which would allow for the use of this compound in synthesis.

Publications

2017

Ledingham, E. T., K. P. Stockton and B. W. Greatrex (2017). Efficient Synthesis of an Indinavir Precursor from Biomass-Derived (–)-Levoglucosenone. Aust. J. Chem. Early Access.

Ledingham, E. T., Merritt, C. J., Sumby, C. J., Taylor, M. K., and B. W.  Greatrex (2017). Stereoselective Cyclopropanation of (–)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides. Synthesis, 49(12): 2652-2662

2016

Stockton, K. P. and B. W. Greatrex (2016). Synthesis of enantiopure cyclopropyl esters from (−)-levoglucosenone. Org. Biomol. Chem. 14(31): 7520-7528.

Sadgrove, N. J., T. L. Collins, S. V.-M. Legendre, J. Klepp, G. L. Jones and B. W. Greatrex (2016). The Iridoid Myodesert-1-ene and Elemol/Eudesmol are found in Distinct Chemotypes of the Australian Aboriginal Medicinal Plant Eremophila dalyana (Scrophulariaceae). Nat. Prod. Commun. 11(9): 1211-1214.

Wilson, K. L., A. R. Kennedy, J. Murray, B. Greatrex, C. Jamieson and A. J. Watson (2016). Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation. Beilstein J. Org. Chem. 12(1): 2005-2011.

Lyddiard, D., G. L. Jones and B. W. Greatrex (2016). Keeping it simple: Lessons from the golden era of antibiotic discovery. FEMS Microbiol. Lett. 363(8).

Peru, A. A. M., A. L. Flourat, C. Gunawan, W. Raverty, M. Jevric, B. W. Greatrex and F. Allais (2016). Chemo-enzymatic synthesis of chiral epoxides ethyl and methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable levoglucosenone: An access to enantiopure (S)-dairy lactone. Molecules 21(8), pii: E988.

2015

Stockton, K. P., C. J. Merritt, C. J. Sumby and B. W. Greatrex (2015). Palladium-Catalyzed Suzuki–Miyaura, Heck and Hydroarylation Reactions on (–)-Levoglucosenone and Application to the Synthesis of Chiral γ-Butyrolactones. Eur. J. Org. Chem. 2015(32): 6999-7008.

Stockton, K. P., S. A. Glover and B. W. Greatrex (2015). Nucleophilic trapping of alkoxy-stabilized oxyallyl systems generated from inosose 2-O-mesylates. Synlett 26(1): 111-115.

Greatrex, B. W., A. M. Daines, S. Hook, D. H. Lenz, W. McBurney, T. Rades and P. M. Rendle (2015). Synthesis, Formulation, and Adjuvanticity of Monodesmosidic Saponins with Olenanolic Acid, Hederagenin and Gypsogenin Aglycones, and some C-28 Ester Derivatives. ChemistryOpen: 740-755.

2014

Stockton, K. P., B. W. Greatrex and D. K. Taylor (2014). Synthesis of allo- and epi-Inositol via the NHC-Catalyzed Carbocyclization of Carbohydrate-Derived Dialdehydes. J. Org. Chem. 79(11): 5088-5096.

Glover, S. A., A. A. Rosser, A. Taherpour and B. W. Greatrex (2014). Formation and heron reactivity of cyclic n,n-dialkoxyamides. Aust. J. Chem. 67(3): 507-520.

Sadgrove, N. J., G. L. Jones and B. W. Greatrex (2014). Isolation and characterisation of (−)-genifuranal: The principal antimicrobial component in traditional smoking applications of Eremophila longifolia (Scrophulariaceae) by Australian Aboriginal peoples. J. Ethnopharmacol. 154(3): 758-766.

Sadgrove, N. J., I. R. H. Telford, B. W. Greatrex and G. L. Jones (2014). Composition and antimicrobial activity of the essential oils from the Phebalium squamulosum species complex (Rutaceae) in New South Wales, Australia. Phytochemistry97: 38-45.

Stockton, K. P., J. P. May, D. K. Taylor and B. W. Greatrex (2014). Practical evaluation of compact fluorescent lamps for dye-sensitized photooxidation reactions. Synlett 25(8): 1168-1172.

2013

Sadgrove, N. J., I. R. H. Telford, B. W. Greatrex, A. Dowell and G. L. Jones (2013). Dihydrotagetone, an unusual fruity ketone, is found in enantiopure and enantioenriched forms in additional Australian native taxa of Phebalium (Rutaceae: Boronieae). Nat. Prod. Commun. 8(6): 737-740.

Research Supervision Experience

In the past five years I have supervised to completion two PhD students and one MSc student and a large number of honours students. I currently supervise four PhD students and so have a vibrant lab with opportunities for motivated students.