Total Synthesis of Biologically Important Natural Products
We 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 Structures
Often 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 Chemistry
Research 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.
We collaborate with the Paddon-Row
group and we are actively involved in the Centre
of Excellence in Free Radical Chemistry.
Click here if you are interested in joining the Sherburn Research Group.
