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| Research Interests |
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Chemistry is, to a great extent, about chemical reactions -- developing
them, understanding them, and using them to make interesting molecules.
Much of the activity in my research group is directed at discovering new
ways to make complex molecules. This includes (a) the design of unique
strategies to particular families of structurally-intricate molecules,
often possessing useful pharmacological properties, or (b) the invention
of new reactions, or the development of useful aspects of known reactions,
particularly their asymmetric variants.
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| With regard to strategies, we have devised concise new routes to several families of natural products. Our route to triquinane natural products, for example, exploits the strain and the dense complexity that is achieved through the intramolecular Paterno-Buchi reaction of 5-acyl-2-norbornenes. Our many successes in this area includes the short, stereocontrolled syntheses of several diverse natural products, including isocomene, hirsutene, and modhephene. Most recently we have completed an exceedingly short synthesis of 5-oxosilphiperfol-6-ene. The Diels-Alder reaction shown in Scheme II is remarkable in that it proceeded with excellent regio, endo, and diastereofacial selectivities to afford a cycloadduct with all the carbons necessary for the natural product. A pivotal Paterno-Buchi reaction followed by selective fragmentation of key bonds and oxidation yielded the natural product. |
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| We also have efforts directed toward the efficient syntheses of several biologically important and structurally complex natural products, some of which are shown below. Our objective is devise short, high yielding syntheses, through strategies that examine interesting aspects of structure and reactivity. |
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We have been actively involved in the development useful synthetic methods.
For example, we have developed several methods for aryl-aryl couplings
using a novel palladacyclic catalyst. In the area of asymmetric synthesis,
we have developed simple, highly-reactive new diene, the chiral version
of which allows the synthesis of substituted cyclohexenones with enantiopurities
as high as 99:1. We are also actively pursuing the design of new methods
for asymmetric synthesis. Finally, we have an active program aimed at the
development of chiral hydrogen bond donor catalysts for asymmetric synthesis. Our interest in this area predates our first publication in this area by several years (click here).
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