Our group is engaged in a variety of projects ranging from total synthesis to investigations of new reactions and the design of enzyme inhibitors. In total synthesis, we work on implementing reliable and efficient routes to target molecules. Our ventures are exact and logical pursuits, yet serendipity, intuition, and art all form an integral part of designing a total synthesis.
Recently we have exploited the biooxidation of aromatic compounds in an exhaustive approach to the synthetic design of carbohydrates and their derivatives. Our guiding principles are symmetry, simplicity, and precise order of operations so that any derivative or stereoisomer with a sugar backbone can be constructed. These products are tested for glycosidase inhibition, a process important in viral expression. In addition, carbocyclic sugars can act as cell messengers, and their availability through synthesis allows greater understanding of cellular communication.
Morphine, pancratistatin, and taxol are other important molecules in which our group has invested much synthetic effort. Their total synthesis permits the investigation of new reactions and mechanistic pathways, which can then be applied in subsequent syntheses.
Finally we are devoting some effort to studies in the mechanism of prokaryotic oxygenase enzymes. Our ultimate goal is the design of a synthetic enzyme mimic that can be used as a chiral reagent for aromatic cis-hydroxylation.
Acta Volume 32, Number 2, 1999
Enzymatic Dihydroxylation of Aromatics in Enantioselective Synthesis: Expanding Asymmetric Methodology