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Research School of Chemistry
Sherburn Research Group
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Synthesis Design and Discovery Associate Professor Mick Sherburn
We develop more efficient ways to access compounds of proven medicinal importance and structures of fundamental significance. We do this by designing new domino reaction sequences: spectacular events in which many new bonds are formed in one synthetic operation. We target synthetically challenging structures and employ unprecedented molecular transformations to access them. The focus of our work is to devise new methods that take the art of chemical synthesis to the next level, rather than simply applying known methods. We target new molecular recognition and catalysis technologies, using state-of-the-art computational methods (through collaboration) to steer our laboratory work. Overall, we strive to develop practical syntheses of complex molecules.
Current research activitiesTotal Synthesis of Biologically Important Natural ProductsWe have developed a novel, efficient and very general way to produce complex polycyclic structures from simple, unsaturated, acyclic precursors using sequences of Diels-Alder reactions. Applications of these processes in total synthesis are being investigated. In 2008 we completed the shortest total synthesis of the natural product triptolide, which shows great potential in medicine due to its myriad biological activities. Lignans like podophyllotoxin have cancer-fighting properties and are used in chemotherapy. An efficient and highly modular approach for the synthesis of lignan natural products has been developed, culminating in several total syntheses, including that of podophyllotoxin. The approach involves a late stage domino radical reaction. Our strategy has several advantages over previous syntheses, the most significant being that it allows a high level of convergency at the end of the synthetic route. Significant progress has also been made towards the natural product viridin, a particularly challenging structure that we have been targeting since 2003. Fascinating New Designed StructuresOften chemists are inspired by nature's chemical structures to develop syntheses. Sometimes, structures not produced naturally initiate the development of exciting new methods, concepts and principles. Our interest in this area is focused on the dendralenes, one of the four fundamental classes of conjugated hydrocarbon structures. We have devised the first chemical synthesis of this hydrocarbon family, previously believed to be too unstable to prepare. Another important development involves the conversion of the dendralenes into the ivyanes, saturated hydrocarbons with helical structures. These findings have led to a better understanding of the stability and reactivity of organic substances. Host-Guest ChemistryResearch in this area is concerned with the design and synthesis of our "superbowl" host molecules for molecular recognition, complexation and catalysis. Superbowls are a new class of synthetic hosts with non-collapsible interiors. Major recent advances include the synthesis of new types of superbowl container molecules with different internal dimensions, which can accommodate different "guests". We have also demonstrated for the first time that superbowl molecules selectively encapsulate medicinal agents. Annual Research Report (PDF format)
Group membersAcademic Staff: PhD Students: MPhil students: Visiting Scholars: Honours Students: Technical Staff:
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Page last updated: 23 October 2008 Please direct all enquiries to: Research School of Chemistry Page authorised by: Director, Research School of Chemistry |
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