School of Physical and Chemical Sciences Te Kura Matū Seminar Series

One Ring To Rule Them All: The synthesis of biologically relevant compounds from cyclopropanes

Speaker

Bill Hawkins

Institute

Senior Lecturer, Department of Chemistry, University of Otago, New Zealand

Time & Place

Wed, 15 May 2019 12:00:00 NZST in Room 701, Level 7, West Building

All are welcome

Abstract

The rich chemical diversity of natural products and their often useful biological activity has provided a wealth of structures that lend themselves to the discovery of potential medicines.In fact, nearly 50% of all clinically used drugs are natural products or directly derived therefrom.1

Our research program is focussed on the development of new synthetic methods and their application to the synthesis of medicinally relevant scaffolds including natural and non-natural compounds.

One central theme within the group is aimed at utilising ring strain to gain access to medicinally privileged scaffolds. This seminar will discuss our efforts to generate highly functionalised oxazinones from various in situ generated N-acyl cyclopropyl iminium ions,2 as well as spring loaded dehydration reactions which provide robust and rapid entry into highly functionalised chromones and benzannulated spiroketals.3

Lastly our efforts to apply this chemistry and others to a series of natural products including berkelic acid,3 bromophycoic acid E,4 isoxycyclointegrin5 and spiroleucettadine6 will be detailed.

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  1. Newman, D.J, Cragg, G. M. J. Nat.Prod. 2016, 79, 629.
  2. a) Craig, A.J.; van der Salm, L.; Stevens-Cullinane, L.; Lucas, N.T.; Tan, E.W.; Hawkins, B.C. Org. Lett. 2015, 17, 234. b) Smith, R.J.; Mills, D.A.; Nhu, D.; Tan, E.W.; Lucas, N.T.; Hawkins, B.C. J. Org. Chem. 2016, 81, 2099.
  3. Gai, S., Lucas, N. T., Hawkins, B. C. Org. Lett. 2019, 21, 2872.
  4. Smith, R.J., Nhu, D., Clark M.P., Gai, S., Lucas, N. T., Hawkins, B.C. J. Org. Chem. 2017, 82, 5317.
  5. Smith, R. J., Bowers, R., Cameron, S., Rosengren, R. J., Cook, G. M., Hawkins, B. C. Eur. J. Org. Chem. 2019, 1571.
  6. a) Lamb, R.A., Aberle, N., Lucas, N.T., Lessene, G., Hawkins B. C. Angew. Chem. Int. Ed. 2017, 56, 14663. b)  Lamb, R.A., Lucas, N.T., Lessene, G., Hawkins B. C. J. Org. Chem. 2018, 83, 10120.

 

All Welcome

Biography

Read more about Bill Hawkins here.