Associate Professor Bill Hawkins, Home

PhD(W'gong), BMedCHem(Hons)

Tel: 03 471 6217
Location: Science II 2n8
Email: bhawkins@chemistry.otago.ac.nz

Bill completed his PhD at the University of Wollongong, followed by postdoctoral positions at the University of Melbourne and Ecole Polytechnique (France). After a short stay at the Walter and Eliza Hall institute for medical research, he joined the Department of Chemistry at the University of Otago as a lecturer (2012) and was promoted to senior lecturer in 2016. His research interests include the synthesis of bioactive natural products and their use as chemical probes to understand biological processes and inform drug design, as well as the development of new synthetic methodologies.

For more information about the Hawkins Research Group: https://blogs.otago.ac.nz/hawkinsgroup/

Publications

Hawkins, B. C., Chalker, J. M., Coote, M. L., & Bissember, A. C. (2024). Electrochemically generated carbocations in organic synthesis. Angewandte Chemie, e202407207. Advance online publication. doi: 10.1002/ange.202407207 Journal - Research Other

Gai, S., Guilder, H. D., & Hawkins, B. C. (2024). Expedient synthesis of [5,5]- and [6,5]-benzannulated spiroketals from 1,1-diacyl-2-vinyl cyclopropanes. Arkivoc, 2024(2), 202312101. doi: 10.24820/ARK.5550190.P012.101 Journal - Research Article

Hawkins, B. C., Bissember, A. C., Wales, S. M., Chen, J. L.-Y., Petersen, W. F., Tague, A. J., … Green, N. J., … Harrison, S. D. L., & Cording, A. P. (2023). Seven-membered rings. In G. W. Gribble & R. A. Aitken (Eds.), Progress in heterocyclic chemistry (Vol. 35). (pp. 569-628). Amsterdam, Netherlands: Elsevier. doi: 10.1016/B978-0-443-21936-8.00015-X Chapter in Book - Research

Henneveld, J. S., Shiri, F., Ariafard, A., Lucas, N. T., Bissember, A. C., & Hawkins, B. C. (2023). Dipole-transmissive 1,3-dipolar cycloadditions for the rapid construction of polycyclic N-heterocycles: Synthetic and mechanistic investigations. Chemistry: A European Journal. Advance online publication. doi: 10.1002/chem.202301254 Journal - Research Article

Watts, B., Berry, M., Bland, A., Badart, M., Hawkins, B., & Ashton, J. (2022). Tumour cell suppression by spiroleucettadine through dual regulation of cell cycle and apoptosis. F1000Research, 11, 1328. doi: 10.12688/f1000research.126754.1 Journal - Research Article

2024

Journal - Research Article

Journal - Research Other

2023

Chapter in Book - Research

Journal - Research Article

2022

Journal - Research Article

Journal - Research Other

Olivier, W. J., Henneveld, J. S., Smith, J. A., Hawkins, B. C., & Bissember, A. C. (2022). Strategies for the synthesis of Stemona alkaloids: An update. Natural Product Reports, 39, 2308-2335. doi: 10.1039/d2np00058j

Conference Contribution - Verbal presentation and other Conference outputs

Lewin, H., Gamble, A., & Hawkins, B. (2022, November). Investigation into self immolative linkers for cancer prodrugs leading to in situ bioactive synthesis. Verbal presentation at the School of Pharmacy Research Day, Dunedin, New Zealand.

Watts, B. A., Berry, M., Bland, A. R., Hawkins, B. C., & Ashton, J. C. (2022, August-September). Tumour cell suppression by Spiroleucettadine through dual regulation of cell cycle and apoptosis. Verbal presentation at the Australasian Society of Clinical and Experimental Pharmacologists and Toxicologists (ASCEPT) NZ Annual Scientific Meeting, Queenstown, New Zealand.

2021

Chapter in Book - Research

Bissember, A. C., Hyland, C. J. T., Wales, S. M., Hawkins, B. C., Chen, J. L.-Y., Fleming, C. L., Cording, A. P., Henneveld, J. S., … Zarfos, S. D. (2021). Seven-membered rings. In G. W. Gribble & J. A. Joule (Eds.), Progress in heterocyclic chemistry (Vol. 33). (pp. 533-581). Amsterdam, The Netherlands: Elsevier. doi: 10.1016/B978-0-323-98410-2.00016-3

Journal - Research Article

Henneveld, J. S., Gilmer, S. C. L., Lucas, N. T., & Hawkins, B. C. (2021). Rapid generation of 2-acyl-4-phenyltetralones from 1,1-diacylphenylcyclopropanes. Asian Journal of Organic Chemistry, 10, 2553-2556. doi: 10.1002/ajoc.202100500

Badart, M. P., Barnes, E. M., Cording, A. P., Gilmer, S. C. L., Billinghurst, I. D., Edupuganti, V. V. S. R., … Bland, A. R., Bower, R. L., Rana, Z., Ferguson, S. A., Opel Reading, H. K., Cook, G. M., Rosengren, R. J., Krause, K. L., Gamble, A. B., Ashton, J. C., & Hawkins, B. C. (2021). Synthesis and biological evaluation of (-) and (+)-spiroleucettadine and analogues. ChemMedChem, 16, 1308-1315. doi: 10.1002/cmdc.202000954

Gai, S., Henneveld, J. S., Cording, A. P., Badart, M. P., Lucas, N. T., & Hawkins, B. C. (2021). The synthesis of benzannulated spiroketals from 1,1-diacyl-2-phenylcyclopropanes. Tetrahedron Letters, 69, 152984. doi: 10.1016/j.tetlet.2021.152984

Philem, P., Kleffmann, T., Gai, S., Hawkins, B. C., Wilbanks, S. M., & Lamont, I. L. (2021). Identification of active site residues of the siderophore synthesis enzyme PvdF and evidence for interaction of PvdF with a substrate-providing enzyme. International Journal of Molecular Sciences, 22(4), 2211. doi: 10.3390/ijms22042211

Journal - Research Other

Badart, M. P., & Hawkins, B. (2021). Synthetic strategies to access heteroatomic spirocentres embedded in natural products. Synthesis, 53, 1683-1705. doi: 10.1055/a-1379-2312

2020

Journal - Research Article

Swaney, B., Luxenburger, A., Lucas, N. T., Hawkins, B. C., & Hinkley, S. F. R. (2020). The synthesis of 3-azabicyclo[4.3.0]nonane scaffolds from Brefeldin A. Tetrahedron Letters, 61, 152006. doi: 10.1016/j.tetlet.2020.152006

Craig, A. J., Cording, A. P., Garden, A. L., & Hawkins, B. C. (2020). Does the reaction of cyclopropyl acid chlorides and imines to form 1, 3-oxazin-4-enone heterocycles proceed via a ketene or an N-acyl-Iminium mechanism? Journal of Organic Chemistry, 85, 5486-5492. doi: 10.1021/acs.joc.0c00229

Journal - Research Other

Craig, A. J., & Hawkins, B. C. (2020). The bonding and reactivity of α-carbonyl cyclopropanes. Synthesis, 52(1), 27-39. doi: 10.1055/s-0039-1690695

2019

Journal - Research Article

Bland, A. R., Bower, R. L., Nimick, M., Hawkins, B. C., Rosengren, R. J., & Ashton, J. C. (2019). Cytotoxicity of curcumin derivatives in ALK positive non-small cell lung cancer. European Journal of Pharmacology, 865, 172749. doi: 10.1016/j.ejphar.2019.172749

Smith, R. J., & Hawkins, B. C. (2019). Synthetic strategies towards the synthesis of oxyisocyclointegrin. European Journal of Organic Chemistry, 40, 6847-6854. doi: 10.1002/ejoc.201901294

Hamiaux, C., Larsen, L., Lee, H. W., Luo, Z., Sharma, P., Hawkins, B. C., Perry, N. B., & Snowden, K. C. (2019). Chemical synthesis and characterization of a new quinazolinedione competitive antagonist for strigolactone receptors with an unexpected binding mode. Biochemical Journal, 476, 1843-1856. doi: 10.1042/bcj20190288

Smith, R. J., Bower, R. L., Ferguson, S. A., Rosengren, R. J., Cook, G. M., & Hawkins, B. C. (2019). The synthesis of (±)-oxyisocyclointegrin. European Journal of Organic Chemistry, (7), 1571-1573. doi: 10.1002/ejoc.201801751

Journal - Research Other

Gai, S., Lucas, N. T., & Hawkins, B. C. (2019). Benzannulated 6,5-spiroketals from donor-acceptor cyclopropanes. Organic Letters, 21(8), 2872-2875. doi: 10.1021/acs.orglett.9b00878

Swaney, B. E., Gai, S., Clark, M. R., & Hawkins, B. C. (2019). Selective mono-allylation of 1,3-diketones and their use in the synthesis of 3-allyl chromones and benzannulated 6,5-bicyclic ketals [Communication]. Chemistry: An Asian Journal, 14, 1102-1105. doi: 10.1002/asia.201801695

2018

Journal - Research Article

Lamb, R. A., Lucas, N. T., Lessene, G., & Hawkins, B. C. (2018). Strategies, setbacks, and successes in the synthesis of (-)-spiroleucettadine. Journal of Organic Chemistry, 83(17), 10120-10133. doi: 10.1021/acs.joc.8b01404

French, S. A., Clark, M. R., Smith, R. J., Brind, T., & Hawkins, B. C. (2018). Expedient synthesis of xanthones and multi-functionalized chromones from 1,1-diacyl cyclopropanes. Tetrahedron, 74(38), 5340-5350. doi: 10.1016/j.tet.2018.04.003

Chen, S., Nimick, M., Cridge, A. G., Hawkins, B. C., & Rosengren, R. J. (2018). Anticancer potential of novel curcumin analogs towards castrate-resistant prostate cancer. International Journal of Oncology, 52(2), 579-588. doi: 10.3892/ijo.2017.4207

Journal - Research Other

Lamb, R. A., Lessene, G., & Hawkins, B. C. (2018). The synthesis of (–)-Spiroleucettadine. Synlett, 29, A-F. doi: 10.1055/s-0036-1591776

Conference Contribution - Poster Presentation (not in published proceedings)

Badart, M. P., Lamb, R. A., Swaney, B. E., Gai, S., Squires, C. M. L., Baird, S. K., & Hawkins, B. C. (2018, August). Synthesis of bioactive natural products. Poster session presented at the Queenstown Molecular Biology (QMB) Meetings, Queenstown, New Zealand.

2017

Journal - Research Article

Lamb, R. A., Aberle, N. S., Lucas, N. T., Lessene, G., & Hawkins, B. C. (2017). Total synthesis of (—)-Spiroleucettadine [Brief communication]. Angewandte Chemie International Edition, 56(46), 14663-14666. doi: 10.1002/anie.201708110

Smith, R. J., Nhu, D., Clark, M. R., Gai, S., Lucas, N. T., & Hawkins, B. C. (2017). Synthesis of chromones from 1,1-diacylcyclopropanes: Toward the synthesis of bromophycoic acid E. Journal of Organic Chemistry, 82(10), 5317-5327. doi: 10.1021/acs.joc.7b00648

Revalde, J. L., Li, Y., Wijeratne, T. S., Budge, P., Hawkins, B. C., Rosengren, R. J., & Paxton, J. W. (2017). Curcumin and its cyclohexanone analogue inhibited human Equilibrative nucleoside transporter 1 (ENT1) in pancreatic cancer cells. European Journal of Pharmacology, 803, 167-173. doi: 10.1016/j.ejphar.2017.03.055

Craig, A. J., & Hawkins, B. C. (2017). Metal-free synthesis of oxazinones and their reductive ring opening to provide cyclopropyl carbinols. Synthesis, 49(9), 1955-1968. doi: 10.1055/s-0036-1588748

Nhu, D., Larsen, L., Perry, N. B., Larsen, D. S., & Hawkins, B. C. (2017). Sweet poisons: Synthetic strategies towards tutin glycosides. Australian Journal of Chemistry, 70(3), 301-306. doi: 10.1071/CH16429

Conference Contribution - Published proceedings: Abstract

Craig, A. J., & Hawkins, B. C. (2017). Preparation of cyclopropyl carbinols via reductive ring opening of ethyl-chloro-oxazinones. Proceedings of the Royal Australian Chemical Institute (RACI) Centenary Congress. (pp. 607). Retrieved from http://www.racicongress.com/

Swaney, B., Clark, M., & Hawkins, B. (2017). Intramolecular Tsuji-Trost reaction: Efficient access to mono-allylated 1,3-diketones. Proceedings of the Royal Australian Chemical Institute (RACI) Centenary Congress. (pp. 543). Retrieved from http://www.racicongress.com/

Smith, R. J., Nhu, D., Clark, M. R., Gai, S., & Hawkins, B. C. (2017). One ring to rule them all: The synthesis of biologically relevant compounds from cyclopropanes. Proceedings of the Royal Australian Chemical Institute (RACI) Centenary Congress. (pp. 371). Retrieved from http://www.racicongress.com/

Lamb, R. A., Lessene, G., & Hawkins, B. C. (2017). Synthetic efforts towards spiroleucettadine. Proceedings of the Royal Australian Chemical Institute (RACI) Centenary Congress. (pp. 352). Retrieved from http://www.racicongress.com/

2016

Chapter in Book - Research

O'Donnell, M. J., Craig, A. J., & Hawkins, B. C. (2016). Ethyl N-(Diphenylmethylene)glycinate. In e-EROS: Encyclopedia of reagents for organic synthesis. (pp. 1-6). Wiley. doi: 10.1002/047084289X.re063m.pub2

Journal - Research Article

Badart, M. P., Squires, C. M. L., Baird, S. K., & Hawkins, B. C. (2016). The synthesis of clavatadine C. Tetrahedron Letters, 57(46), 5108-5111. doi: 10.1016/j.tetlet.2016.10.019

Smith, R. J., Mills, D. A., Nhu, D., Tan, E. W., Lucas, N. T., & Hawkins, B. C. (2016). The synthesis of multifunctionalized 1,3-oxazin-4-ones from donor-acceptor cyclopropanes. Journal of Organic Chemistry, 81(5), 2099-2105. doi: 10.1021/acs.joc.6b00112

Chiluka, R., Gamble, A. B., Lucas, N. T., Hawkins, B. C., Bhumkar, A., Achanta, P. S., & Bobbala, R. K. (2016). Flavone C-glycosides from Trichuriella monsoniae (L.f.) Bennet. Natural Product Research. doi: 10.1080/14786419.2016.1149707

Conference Contribution - Published proceedings: Abstract

Lamb, R., & Hawkins, B. (2016). Synthetic studies towards spiroleucettadine. Proceedings of the 251st American Chemical Society (ACS) National Spring Meeting. Retrieved from https://www.acs.org

Hawkins, B. (2016). Expedient synthesis of 1,3-oxazinenones. Proceedings of the 251st American Chemical Society (ACS) National Spring Meeting. Retrieved from https://www.acs.org

Gwavava, P., Nimick, M., Taurin, S., Hawkins, B. C., & Rosengren, R. J. (2016). The curcumin derivative RL112 induces apoptosis in ovarian cancer cells. The Toxicologist. (pp. 75-76). [Abstract]

Petersen, J., Lamb, R. A., Badart, M. P., Hawkins, B. C., & Baird, S. K. (2016). Anticancer effects of novel 4-substituted phenylthiazoles derived from marine actinomycetes. Proceedings of the Diagnostics, Drugs, Devices, Discovery (D4) Conference. Retrieved from http://www.otago.ac.nz/d4/index.html

Craig, A., Smith, R., Stevens-Cullinane, L., Lucas, N. T., Tan, E. W., & Hawkins, B. C. (2016). The synthesis of multifunctionalised 1,3-oxazin-4-Enones from 1-acyl-1-cyclopropyl carboxylic acids. Proceedings of the Diagnostics, Drugs, Devices, Discovery (D4) Conference. Retrieved from http://www.otago.ac.nz/d4/index.html

Swaney, B., Williams, B., Hinkley, S., & Hawkins, B. (2016). Design and synthesis of Brefeldin A analogues. Proceedings of the Diagnostics, Drugs, Devices, Discovery (D4) Conference. Retrieved from http://www.otago.ac.nz/d4/index.html

Swaney, B. E., Williams, B. G., Hinkley, S. F., & Hawkins, B. C. (2016). Design and synthesis of Brefeldin A analogues. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Retrieved from http://www.nzic16.org/

Smith, R. J., Craig, A. J., Tan, E. W., Lucas, N. T., & Hawkins, B. C. (2016). Expedient synthesis of 1,3-oxazin-4-ones. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Retrieved from http://www.nzic16.org/

Larsen, L., Joyce, N. I., Sansom, C. E., Cooney, J. M., Jensen, D. J., Watkins, O. C., … Nhu, D., Hawkins, B. C., & Perry, N. B. (2016). Sweet poisons: Discovery, source and synthesis of neurotoxin tutin glycosides in New Zealand honeys. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Retrieved from http://www.nzic16.org/

Craig, A. J., Smith, R., Stevens-Cullinane, L., Lucas, N. T., Tan, E. W., & Hawkins, B. C. (2016). The synthesis of multifunctionalised 1,3-oxazin-4-enones from 1-acyl-1-cyclopropyl carboxylic acids. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Retrieved from http://www.nzic16.org/

Megna, B., Carney, P., Depke, M., Rosengren, R., Hawkins, B., & Kennedy, G. (2016). Chemotherapeutic action of synthetic curcumin analogs in colorectal cancer. Diseases of the Colon & Rectum, 59(5), (pp. e74). doi: 10.1097/01.dcr.0000482708.50838.af

Conference Contribution - Verbal presentation and other Conference outputs

Smith, R., Craig, A., Clark, M., & Hawkins, B. (2016, August-September). One ring to rule them all: The synthesis of biologically relevant compounds from cyclopropanes. Verbal presentation at the Queenstown Molecular Biology (QMB) Meetings, Nelson, New Zealand.

2015

Journal - Research Article

Lamb, R. A., Badart, M. P., Swaney, B. E., Gai, S., Baird, S. K., & Hawkins, B. C. (2015). The synthesis and biological evaluation of anithiactin A/thiasporine C and analogues. Australian Journal of Chemistry, 68(12), 1829-1833. doi: 10.1071/CH15461

Lei, J., Burgess, E. J., Richardson, A. T. B., Hawkins, B. C., Baird, S. K., Smallfield, B. M., van Klink, J. W., & Perry, N. B. (2015). Cytotoxic amides from fruits of kawakawa, Macropiper excelsum. Planta Medica, 81, 1163-1168. doi: 10.1055/s-0035-1546106

Nhu, D., Hawkins, B. C., & Burns, C. J. (2015). Phase transfer catalysis extends the scope of the Algar—Flynn—Oyamada synthesis of 3-hydroxyflavones. Australian Journal of Chemistry, 68, 1102-1107. doi: 10.1071/CH14620

Revalde, J. L., Li, Y., Hawkins, B. C., Rosengren, R. J., & Paxton, J. W. (2015). Heterocyclic cyclohexanone monocarbonyl analogues of curcumin can inhibit the activity of ATP-binding cassette transporters in cancer multidrug resistance. Biochemical Pharmacology, 93(3), 305-317. doi: 10.1016/j.bcp.2014.12.012

Craig, A. J., van der Salm, L., Stevens-Cullinane, L., Lucas, N. T., Tan, E. W., & Hawkins, B. C. (2015). Expedient metal-free synthesis of 1,3-oxazinen-4-ones. Organic Letters, 17(2), 234-237. doi: 10.1021/ol503350h

Conference Contribution - Verbal presentation and other Conference outputs

Lamb, R., Lessene, G., & Hawkins, B. (2015, April). Synthetic strategies towards the synthesis of spiroleucettadine. Verbal presentation at the SynthCon3 Meeting, Yarra Glen, Australia.

2014

Journal - Research Article

Hawkins, B. C., Lindqvist, L. M., Nhu, D., Sharp, P. P., Segal, D., Powell, A. K., … Burns, C. J. (2014). Simplified silvestrol analogues with potent cytotoxic activity. ChemMedChem, 9, 1556-1566. doi: 10.1002/cmdc.201400024

Stevens-Cullinane, L., Lucas, N. T., & Hawkins, B. C. (2014). Sterically controlled Diels–Alder cycloadditions: Rapid entry into the illudin scaffold. European Journal of Organic Chemistry, 2014(22), 4767-4772. doi: 10.1002/ejoc.201402461

Conference Contribution - Verbal presentation and other Conference outputs

Hawkins, B., & Stevens-Cullinane, L. (2014, December). Synthetic strategies towards the illudin sesquiterepenes. Verbal presentation at the Royal Australian Chemical Institute (RACI) National Congress, Adelaide, Australia.

2013

Journal - Research Article

Birkett, S., Ganame, D., Hawkins, B. C., Meiries, S., Quach, T., & Rizzacasa, M. A. (2013). Total synthesis of the proposed structure of 8-deshydroxyajudazol A: A modified approach to 2,4-disubstituted oxazoles. Journal of Organic Chemistry, 78, 116-123. doi: 10.1021/jo302055w

Conference Contribution - Published proceedings: Abstract

Hawkins, W. C., & Stevens-Cullinane, L. (2013). Synthetic strategies towards the Illudin sesquiterpenes. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Christchurch, New Zealand: NZIC. [Abstract]

Conference Contribution - Verbal presentation and other Conference outputs

Hawkins, B. (2013, September). The synthesis of biologically active compounds and their use as tools in medicinal chemistry. Verbal presentation at the Ozone Research Group Public Symposium, Dunedin, New Zealand.

2012

Journal - Research Article

Hawkins, B., Paddock, V. L., Tölle, N., & Zard, S. Z. (2012). A convenient conversion of terminal alkenes into homologous unsaturated and doubly unsaturated esters. Organic Letters, 14(4), 1020-1023. doi: 10.1021/ol203387r