Dr Christopher McErlean

BSc PhD UQ
Senior Lecturer

F11 - Chemistry Building
The University of Sydney

Telephone 61 2 9351 3970
Fax 61 2 9351 3329

Website Contact Details
McErlean Research Group

Biographical details

  • B.Sc.(Hons I), University of Queensland, 1997
  • Ph.D. University of Queensland, 2002
  • Postdoctoral Research Associate, Nottingham, 2002-2004
  • Postdoctoral Research Fellow, Exeter / Nottingham , 2004-2007
  • Teaching Fellow in Organic Chemistry, Nottingham, 2006-2007
  • Lecturer, University of Sydney, 2007-2011
  • Senior Lecturer, University of Sydney, 2012 -

Research interests

  • Synthetic Organic Chemistry
  • Reaction development
  • Total synthesis

We are interested in developing new reactions, and applying known reactions in novel ways, in an effort to reduce the complexity of natural product synthesis.

Expanding the scope of the Stetter reaction: The 'umpolung' addition of aldehydes onto unsaturated carbonyl compounds is an under-utilised method for carbon-carbon bond construction. We are investigating variants of this reaction that allow for the rapid construction of fused-ring systems from simple starting materials. We are also exploring the ability of the Stetter reaction to install new stereocentres under substrate control.

Palladium-catalysed tetrahydrofuran synthesis: Numerous natural products and biologically active compounds contain a substituted tetrahydrofuran unit. We are employing a short, high-yielding, palladium-catalysed protocol to synthesis a series of these natural products.

Ligand design for new reactions: Mimicking nature's ability to incorporate stereogenic elements into substrate compounds is a major driving force in contemporary chemistry. We are involved in the rational design and efficient synthesis of ligands that will allow new reactions to be accomplished.

Visit the McErlean Research Group at http://sydney.edu.au/science/chemistry/~mcerlean

Selected grants

2014

  • University of Sydney Automated Peptide Synthesis Platform; Payne R, Britton W, Byrne S, Chan H, Clarke R, Hunt N, Jolliffe K, Kassiou M, Lay P, Mackay J, Matthews J, McErlean C, New E, Rasmussen H, Rendina L, Rudrawar S, Rutledge P, Shepherd N; National Health and Medical Research Council (NHMRC)/Equipment Grants.

2013

  • Strigologues: Inventing activity-specific plant hormones.; McErlean C, Yoneyama K; Australian Research Council (ARC)/Discovery Projects (DP).

2012

  • Nucleophilic Catalysis for Asymmetric Halogenation and Synthetic Applications; Recsei C, McErlean C; Australia - Israel Scientific Exchange Foundation/Research Support.
  • On-Water Catalysis for Green Chemistry; Beattie J, McErlean C; Australian Research Council (ARC)/Discovery Projects (DP).

Selected publications

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Journals

  • Kim, H., Kisugi, T., Khetkam, P., Xie, X., Yoneyama, K., Uchida, K., Yokota, T., Nomura, T., McErlean, C., Yoneyama, K. (2014). Avenaol, a germination stimulant for root parasitic plants from Avena strigosa. Phytochemistry, 103, 85-88. [More Information]
  • Eyre, N., Fiches, G., Aloia, A., Helbig, K., McCartney, E., McErlean, C., Li, K., Aggarwal, A., Turville, S., Beard, M. (2014). Dynamic imaging of the hepatitis C virus NS5A protein during a productive infection. Journal of Virology, 88(7), 3636-3652. [More Information]
  • Bromhead, L., Visser, J., McErlean, C. (2014). Enantioselective synthesis of the strigolactone mimic (positive) negative GR24. The Journal of Organic Chemistry, 79(3), 1516-1520. [More Information]
  • Recsei, C., Chan, B., McErlean, C. (2014). Synthesis of (+)-Luzofuran and (-) Ancistrofuran. The Journal of Organic Chemistry, 79(3), 880-887. [More Information]
  • Norcott, P., McErlean, C. (2014). Total synthesis of (-)-heliespirone A and (+)-heliespirone C. European Journal of Organic Chemistry, 2014 (23), 5056-5062. [More Information]
  • Beinat, C., Banister, S., McErlean, C., Kassiou, M. (2013). A practical synthesis of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane. Tetrahedron Letters, 54(39), 5345-5347. [More Information]
  • Beare, K., McErlean, C. (2013). Accessing columbianetin-containing natural products via a domino on-water, in-water process. Tetrahedron Letters, 54(9), 1056-1058. [More Information]
  • Law, K., McErlean, C. (2013). Extending the Stetter reaction with 1,6-acceptors. Chemistry: A European Journal, 19(47), 15852-15855. [More Information]
  • Beare, K., Yuen, A., Masters, A., Maschmeyer, T., McErlean, C. (2013). Ionic liquids are compatible with on-water catalysis. Chemical Communications, 49(75), 8347-8349. [More Information]
  • Beare, K., McErlean, C. (2013). Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of 'on-water' catalysis. Organic and Biomolecular Chemistry, 11(15), 2452-2459. [More Information]
  • Cochrane, J., Yoon, D., McErlean, C., Jolliffe, K. (2012). A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues. Beilstein Journal of Organic Chemistry, 8, 1344-1351. [More Information]
  • Norcott, P., Spielman, C., McErlean, C. (2012). An in-water, on-water domino process for synthesis. Green Chemistry, 14(3), 605-609. [More Information]
  • Goldys, A., McErlean, C. (2012). N-acylpyrroles: More than amides. European Journal of Organic Chemistry, 2012 (10), 1877-1888. [More Information]
  • Recsei, C., McErlean, C. (2012). Synthesis of modified binol-phosphoramidites. Tetrahedron, 68(2), 464-480. [More Information]
  • Phippen, C., McErlean, C. (2011). A 1,5-benzothiazepine synthesis. Tetrahedron Letters, 52(13), 1490-1492. [More Information]
  • Phippen, C., Goldys, A., McErlean, C. (2011). Stetter Reactions of Unsaturated 1-acyl-1H-pyrroles. European Journal of Organic Chemistry, 2011 (34), 6957-6964. [More Information]
  • Nesbitt, C., McErlean, C. (2011). Total synthesis of C19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran. Organic and Biomolecular Chemistry, 9(7), 2198-2208. [More Information]
  • Phippen, C., Beattie, J., McErlean, C. (2010). "On-water" conjugate additions of anilines. Chemical Communications, 46(43), 8234-8236.
  • Beinat, C., Banister, S., Moussa, I., Reynolds, A., McErlean, C., Kassiou, M. (2010). Insights into structure-activity relationships and CNS therapeutic applications of NR2B selective antagonists. Current Medicinal Chemistry, 17(34), 4166-4190. [More Information]
  • Beattie, J., McErlean, C., Phippen, C. (2010). The mechanism of on-water catalysis. Chemistry: A European Journal, 16(30), 8972-8974. [More Information]
  • Cochrane, J., McErlean, C., Jolliffe, K. (2010). Total synthesis and assignment of the side chain stereochemistry of LI-F04a: An antimicrobial cyclic depsipeptide. Organic Letters, 12(15), 3394-3397.
  • Recsei, C., McErlean, C. (2010). Towards the synthesis of N-heterocycle containing BINOL-phosphoramidites. Tetrahedron-Asymmetry, 21(2), 149-152.
  • Goldys, A., McErlean, C. (2009). An efficient synthesis of 3,3'-dipyridyl BINOL ligands. Tetrahedron Letters, 50(27), 3985-3987.
  • Nesbitt, C., McErlean, C. (2009). An expedient synthesis of 2,5-disubstituted-3-oxygenated tetrahydrofurans. Tetrahedron Letters, 50(46), 6318-6320.
  • McErlean, C., Willis, A. (2009). Application of an intramolecular Stetter reaction to access trans,syn,trans-fused pyrans. Synlett, 2009 (2), 233-236.
  • Sperry, J., McErlean, C., Slawin, A., Moody, C. (2007). A biomimetic synthesis of calothrixin B. Tetrahedron Letters, 48(2), 231-234.
  • McErlean, C., Moody, C. (2007). First synthesis of N-(3-carboxylpropl)-5-amino-2-hydroxy-3-tridecyl-1,4-benzoquinone, an unusual quinone isolated from Embelia ribes. The Journal of Organic Chemistry, 72(26), 10298-10301.
  • McErlean, C., Sperry, J., Blake, A., Moody, C. (2007). Synthesis of the calothrixins, pentacyclic indolo[3,2-j]-phenanthridine alkaloids, using a biomimetc approach. Tetrahedron, 63(45), 10963-10970.
  • McErlean, C., Proisy, N., Davis, C., Boland, N., Sharp, S., Boxall, K., Slawin, A., Workman, P., Moody, C. (2007). Synthetic ansamycins prepared by a ring-expanding Claisen rearrangement. Synthesis and biological evaluation of ring and conformational analogues of the Hsp90 molecular chaperone inhibitor geldanamycin. Organic and Biomolecular Chemistry, 5(3), 531-546.
  • Clark, J., Kimber, M., Robertson, J., McErlean, C., Wilson, C. (2005). Rapid two-directional synthesis of the F-J fragment of the gambieric acids by iterative double ring-closing metathesis. Angewandte Chemie (International Edition), 44(38), 6157-6162. [More Information]
  • Schwartz, B., McErlean, C., Fletcher, M., Mazomenos, B., Konstantopoulou, M., Kitching, W., De Voss, J. (2005). Spiroacetal Biosynthesis: (±)-1,7-Dioxaspiro[5.5]undecane in Bactrocera cacuminata and Bactrocera oleae (Olive Fruit Fly). Organic Letters, 7(6), 1173-1176.
  • Hayes, P., Fletcher, M., Chow, S., McGrath, M., Tu, Y., Zhang, H., Hungerford, N., McErlean, C., Stok, J., Moore, C., et al (2003). Insect chemistry and chirality. Chirality, 2003 (15 (Suppl.)), S116-S127. [More Information]
  • McErlean, C., Fletcher, M., Wood, B., De Voss, J., Kitching, W. (2002). Monooxygenase stereoselectivity in the biosynthesis of stereoisomeric spiroacetals in the cucumber fly, bactrocera cucumis. Organic Letters, 4(16), 2775-2778.
  • Gallagher, P., McErlean, C., Jacobs, M., Watters, D., Kitching, W. (2002). Sub-structure syntheses and relative stereochemistry in the bistramide (bistratene) series of marine metabolites. Tetrahedron Letters, 43(3), 531-535.

Conferences

  • Beattie, J., Cagnes, M., Goldys, A., McErlean, C., Phippen, C. (2012). On-water catalysis explained. 3rd Asia-Oceania Conference on Green & Sustainable Chemistry, Australia: Online.
  • McErlean, C., Beattie, J., Phippen, C. (2010). The mechanism of on-water catalysis. The Royal Australian Chemical Institute's National Convention in Conjection with the 12th IUPAC International Congress of Pesticide Chemistry, Australia: RACI.
  • Cochrane, J., McErlean, C., Jolliffe, K. (2009). A macrolactonisation approach to the LI-F antifungal cyclic peptides. 16th European Symposium on Organic Chemistry. N/A.
  • Nesbitt, C., McErlean, C. (2009). An expedient synthesis of 2,5-disubstituted-3-oxygenated tetrahydrofurans. RACI NSW Natural Products Groups Annual One-day Symposium, Sydney, Australia: Royal Australian Chemical Institute.

Patents

  • Ross, D., Siegel, D., Guo, W., Moody, C., McErlean, C. (2009). Patent No. WO2009026548.

2014

  • Kim, H., Kisugi, T., Khetkam, P., Xie, X., Yoneyama, K., Uchida, K., Yokota, T., Nomura, T., McErlean, C., Yoneyama, K. (2014). Avenaol, a germination stimulant for root parasitic plants from Avena strigosa. Phytochemistry, 103, 85-88. [More Information]
  • Eyre, N., Fiches, G., Aloia, A., Helbig, K., McCartney, E., McErlean, C., Li, K., Aggarwal, A., Turville, S., Beard, M. (2014). Dynamic imaging of the hepatitis C virus NS5A protein during a productive infection. Journal of Virology, 88(7), 3636-3652. [More Information]
  • Bromhead, L., Visser, J., McErlean, C. (2014). Enantioselective synthesis of the strigolactone mimic (positive) negative GR24. The Journal of Organic Chemistry, 79(3), 1516-1520. [More Information]
  • Recsei, C., Chan, B., McErlean, C. (2014). Synthesis of (+)-Luzofuran and (-) Ancistrofuran. The Journal of Organic Chemistry, 79(3), 880-887. [More Information]
  • Norcott, P., McErlean, C. (2014). Total synthesis of (-)-heliespirone A and (+)-heliespirone C. European Journal of Organic Chemistry, 2014 (23), 5056-5062. [More Information]

2013

  • Beinat, C., Banister, S., McErlean, C., Kassiou, M. (2013). A practical synthesis of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane. Tetrahedron Letters, 54(39), 5345-5347. [More Information]
  • Beare, K., McErlean, C. (2013). Accessing columbianetin-containing natural products via a domino on-water, in-water process. Tetrahedron Letters, 54(9), 1056-1058. [More Information]
  • Law, K., McErlean, C. (2013). Extending the Stetter reaction with 1,6-acceptors. Chemistry: A European Journal, 19(47), 15852-15855. [More Information]
  • Beare, K., Yuen, A., Masters, A., Maschmeyer, T., McErlean, C. (2013). Ionic liquids are compatible with on-water catalysis. Chemical Communications, 49(75), 8347-8349. [More Information]
  • Beare, K., McErlean, C. (2013). Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of 'on-water' catalysis. Organic and Biomolecular Chemistry, 11(15), 2452-2459. [More Information]

2012

  • Cochrane, J., Yoon, D., McErlean, C., Jolliffe, K. (2012). A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues. Beilstein Journal of Organic Chemistry, 8, 1344-1351. [More Information]
  • Norcott, P., Spielman, C., McErlean, C. (2012). An in-water, on-water domino process for synthesis. Green Chemistry, 14(3), 605-609. [More Information]
  • Goldys, A., McErlean, C. (2012). N-acylpyrroles: More than amides. European Journal of Organic Chemistry, 2012 (10), 1877-1888. [More Information]
  • Beattie, J., Cagnes, M., Goldys, A., McErlean, C., Phippen, C. (2012). On-water catalysis explained. 3rd Asia-Oceania Conference on Green & Sustainable Chemistry, Australia: Online.
  • Recsei, C., McErlean, C. (2012). Synthesis of modified binol-phosphoramidites. Tetrahedron, 68(2), 464-480. [More Information]

2011

  • Phippen, C., McErlean, C. (2011). A 1,5-benzothiazepine synthesis. Tetrahedron Letters, 52(13), 1490-1492. [More Information]
  • Phippen, C., Goldys, A., McErlean, C. (2011). Stetter Reactions of Unsaturated 1-acyl-1H-pyrroles. European Journal of Organic Chemistry, 2011 (34), 6957-6964. [More Information]
  • Nesbitt, C., McErlean, C. (2011). Total synthesis of C19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran. Organic and Biomolecular Chemistry, 9(7), 2198-2208. [More Information]

2010

  • Phippen, C., Beattie, J., McErlean, C. (2010). "On-water" conjugate additions of anilines. Chemical Communications, 46(43), 8234-8236.
  • Beinat, C., Banister, S., Moussa, I., Reynolds, A., McErlean, C., Kassiou, M. (2010). Insights into structure-activity relationships and CNS therapeutic applications of NR2B selective antagonists. Current Medicinal Chemistry, 17(34), 4166-4190. [More Information]
  • McErlean, C., Beattie, J., Phippen, C. (2010). The mechanism of on-water catalysis. The Royal Australian Chemical Institute's National Convention in Conjection with the 12th IUPAC International Congress of Pesticide Chemistry, Australia: RACI.
  • Beattie, J., McErlean, C., Phippen, C. (2010). The mechanism of on-water catalysis. Chemistry: A European Journal, 16(30), 8972-8974. [More Information]
  • Cochrane, J., McErlean, C., Jolliffe, K. (2010). Total synthesis and assignment of the side chain stereochemistry of LI-F04a: An antimicrobial cyclic depsipeptide. Organic Letters, 12(15), 3394-3397.
  • Recsei, C., McErlean, C. (2010). Towards the synthesis of N-heterocycle containing BINOL-phosphoramidites. Tetrahedron-Asymmetry, 21(2), 149-152.

2009

  • Ross, D., Siegel, D., Guo, W., Moody, C., McErlean, C. (2009). Patent No. WO2009026548.
  • Cochrane, J., McErlean, C., Jolliffe, K. (2009). A macrolactonisation approach to the LI-F antifungal cyclic peptides. 16th European Symposium on Organic Chemistry. N/A.
  • Goldys, A., McErlean, C. (2009). An efficient synthesis of 3,3'-dipyridyl BINOL ligands. Tetrahedron Letters, 50(27), 3985-3987.
  • Nesbitt, C., McErlean, C. (2009). An expedient synthesis of 2,5-disubstituted-3-oxygenated tetrahydrofurans. RACI NSW Natural Products Groups Annual One-day Symposium, Sydney, Australia: Royal Australian Chemical Institute.
  • Nesbitt, C., McErlean, C. (2009). An expedient synthesis of 2,5-disubstituted-3-oxygenated tetrahydrofurans. Tetrahedron Letters, 50(46), 6318-6320.
  • McErlean, C., Willis, A. (2009). Application of an intramolecular Stetter reaction to access trans,syn,trans-fused pyrans. Synlett, 2009 (2), 233-236.

2007

  • Sperry, J., McErlean, C., Slawin, A., Moody, C. (2007). A biomimetic synthesis of calothrixin B. Tetrahedron Letters, 48(2), 231-234.
  • McErlean, C., Moody, C. (2007). First synthesis of N-(3-carboxylpropl)-5-amino-2-hydroxy-3-tridecyl-1,4-benzoquinone, an unusual quinone isolated from Embelia ribes. The Journal of Organic Chemistry, 72(26), 10298-10301.
  • McErlean, C., Sperry, J., Blake, A., Moody, C. (2007). Synthesis of the calothrixins, pentacyclic indolo[3,2-j]-phenanthridine alkaloids, using a biomimetc approach. Tetrahedron, 63(45), 10963-10970.
  • McErlean, C., Proisy, N., Davis, C., Boland, N., Sharp, S., Boxall, K., Slawin, A., Workman, P., Moody, C. (2007). Synthetic ansamycins prepared by a ring-expanding Claisen rearrangement. Synthesis and biological evaluation of ring and conformational analogues of the Hsp90 molecular chaperone inhibitor geldanamycin. Organic and Biomolecular Chemistry, 5(3), 531-546.

2005

  • Clark, J., Kimber, M., Robertson, J., McErlean, C., Wilson, C. (2005). Rapid two-directional synthesis of the F-J fragment of the gambieric acids by iterative double ring-closing metathesis. Angewandte Chemie (International Edition), 44(38), 6157-6162. [More Information]
  • Schwartz, B., McErlean, C., Fletcher, M., Mazomenos, B., Konstantopoulou, M., Kitching, W., De Voss, J. (2005). Spiroacetal Biosynthesis: (±)-1,7-Dioxaspiro[5.5]undecane in Bactrocera cacuminata and Bactrocera oleae (Olive Fruit Fly). Organic Letters, 7(6), 1173-1176.

2003

  • Hayes, P., Fletcher, M., Chow, S., McGrath, M., Tu, Y., Zhang, H., Hungerford, N., McErlean, C., Stok, J., Moore, C., et al (2003). Insect chemistry and chirality. Chirality, 2003 (15 (Suppl.)), S116-S127. [More Information]

2002

  • McErlean, C., Fletcher, M., Wood, B., De Voss, J., Kitching, W. (2002). Monooxygenase stereoselectivity in the biosynthesis of stereoisomeric spiroacetals in the cucumber fly, bactrocera cucumis. Organic Letters, 4(16), 2775-2778.
  • Gallagher, P., McErlean, C., Jacobs, M., Watters, D., Kitching, W. (2002). Sub-structure syntheses and relative stereochemistry in the bistramide (bistratene) series of marine metabolites. Tetrahedron Letters, 43(3), 531-535.

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