Organic Synthesis, Methodology and Host-Guest Chemistry Associate Professor Mick Sherburn

Cascade (domino) reactions are spectacular events in which many bonds are made and broken in a single step. These reactions hold much promise for achieving more efficient syntheses: a pressing need in times of increasing production costs and the importance of protecting the environment by reducing waste.

Our research involves the design and implementation of cascading sequences of cycloaddition reactions, free radical reactions and transition metal-mediated reactions to prepare polycyclic molecules with important biological properties.

We also target new ways to improve molecular recognition, bond formation and catalysts. Our goal is to develop practical means for synthesising complex molecules.

Current research activities

Efficient total synthesis of anti-tumour and anti-Alzheimer’s natural products

We are developing efficient modular strategies for synthesis of natural products. Molecules being investigated include lignans like podophyllotoxin which have cancer-fighting properties and are used in chemotherapy. We are also interested in himbacine, a product isolated from Galbulimima baccata, a tree found in Northern Australia. Himbacine and its analogues may be useful for treating degenerative disorders such as Alzheimer’s disease.

Host-Guest chemistry

We are designing and synthesising host molecules based on cavitands - rigid, bowl-shaped molecules. These molecules are designed to selectively hold specific guest molecules. They may prove useful as molecular sized devices for applications such as improved drug delivery or removal of pesticide residues from the environment.

Developing new synthesis methods

We are studying in depth some of the most commonly used reactions in synthetic organic chemistry to better explain, predict, and control the stereochemical outcomes of these reactions. This will aid in developing new, more efficient ways of synthesising complex molecules, for example the synthesis of polycyclic molecules from simple unsaturated acyclic precursors.

Annual Research Report   (PDF format)

Group members

Academic Staff:
Associate Professor Mick Sherburn (Leader)     |   Laurence Kwan   |   Alistair Longshaw   |   Ignace Louis   |   Alan Payne   |   Emma Pearson   |   Diane Robinson

PhD Students:
Gomotsang Bojase-Moleta   |   Tanya Bradford   |   Lucinda Carpinelli   |   Thomas Fallon   |   Catherine Gray   |   Nicholas Kanizaj   |   William Lording   |   Thanh Vinh Nguyen   |   Emma Wiadrowski

Technical Staff:
Dr Natalie Miller

Key publications

1. S. Fielder, D.D. Rowan, M.S. Sherburn, The First Synthesis of the [n]Dendralene Family of Fundamental Hydrocarbons. Angew. Chem. Int. Ed. 2000, 39, 4331-4333.
2. M. Nörret, M.S. Sherburn, The Zipper-Mode Domino IMDA Reaction: A New 0—>ABCD Strategy For Steroids and Related Compounds. Angew. Chem. Int. Ed. 2001, 40, 4074-4076.
3. J. Reynolds, A. J. Scott, C. I. Turner, M. S. Sherburn, The Intramolecular Carboxyarylation Approach to Podophyllotoxin. J. Am. Chem. Soc. 2003, 125, 12108-12109.
4. E. S. Barrett, J. L. Irwin, A. J. Edwards, M. S. Sherburn, Superbowl Container Molecules, J. Am. Chem. Soc. 2004, 126, 16747-16749.
5. A. D. Payne, A. C. Willis, M. S. Sherburn, Practical Synthesis and Diels-Alder Chemistry of [4]Dendralene, J. Am. Chem. Soc. 2005, 127, 12188-12189.

>>more publications

private web page: http://rsc.anu.edu.au/~sherburn/ group photos

Associate Professor M S Sherburn Research School of Chemistry, Building 35 Australian National University Canberra ACT 0200 AUSTRALIA Ph: +61 2 6125 4988 Fx: +61 2 6125 8114 E-mail: sherburn@rsc.anu.edu.au