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.
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.