Department of Chemistry at Illinois State University

Faculty Disciplines - Organic Chemistry Faculty

John F. Hansen
Professor
B.S. 1964, University of Wisconsin-River Falls; Ph.D. 1969, Duke University
Current research interests are in the area of synthetic organic chemistry, particularly the preparation, characterization, and reactions of novel heterocyclic compounds. Areas of interest include studies in the preparation and reactions of novel N-oxygenated pyrazoles and investigation of new 4-oximino-4,5-dihydroisoxazole compounds.

Shawn R. Hitchcock
Professor
B.S. 1990, Wayne State University; Ph.D. 1995, University of California, Davis
Research in the Hitchcock group is primarily focused on developing new methods for synthesizing medicinal agents that exist as single isomer drugs via chiral auxiliaries and chiral catalysts. The rational design, synthesis, and application of chiral auxiliaries and catalysts continues to be an important facet of synthetic organic chemistry. We are very interested in the development of chiral auxiliaries derived from alkaloids of the genus Ephedra. These alkaloids include ephedrine, pseudoephedrine, norephedrine, and pseudonorephedrine. Using the Ephedra alkaloids as chiral templates we have synthesized compounds known as oxadiazinones and applied them in the asymmetric aldol reaction. We have also synthesized a variety of chiral, nonracemic ligands for application in the catalytic asymmetric addition of diethylzinc to aldehydes. Our most recent work involves the successful application of the Ephedra alkaloids in the Tsuji-Trost enantioselective palladium catalyzed allylic alkylation. Using these processes, we have completed the synthesis of the calcimimetic agent NPS R-568 and are working other calcimimetic agents and medicinal agents such as the antiarrhythmic agent sotalol.

Timothy D. Lash
Distinguished Professor
B.S. 1975, University of Exeter; M.Sc. 1977, University College, Cardiff, Wales; Ph.D. 1979, University College, Cardiff, Wales
The Lash laboratory is developing new synthetic routes to macrocyclic compounds such as porphyrins and [18]Annulenes. Projects are directed at the synthesis of both natural systems and unique species with novel spectroscopic and chemical properties. In addition synthetic porphyrin samples have been used as probes for the substrate specificity of the heme biosynthetic enzymes, work that has clinical significance in relation to diseases of porphyrin metabolism. However the major emphasis of investigations involves the synthesis of modified porphyrin structures with fused aromatic rings and/or modified subunits.

T. Andrew Mitchell
Assistant Professor
B.S. 2001, Grove City College (PA); Ph.D. 2008, Texas A&M University
The Mitchell research group is focused on the development of novel synthetic methods and the total synthesis of natural products. One synthetic method is the development of an enantioselective [5+2] cycloaddition toward bridged ethers, which are found in many fascinating classes of natural products and are uniquely accessible with this cycloaddition. An interesting natural product, muironolide A, was isolated from the same sponge that produced the highly active (anticancer) phorboxazole A. Less than 90 μg of muironolide A remains available for biological testing leaving total synthesis as the only viable route to a complete biological profile.

Richard W. Nagorski
Associate Professor
B.S. 1988, Brandon University; Ph.D. 1994, University of Alberta
Carbinolamides are a functional group that are of increasing importance due to their critical presence in a growing number of compounds having interesting biological function. Little is known about the reactivity of this functionality and our studies are designed to probe both the mechanism of reaction and reaction catalysis for these compounds as a function of pH, [buffer], and [metal-ion]. The goal of the studies is to elucidate the reaction pathways of carbinolamides and carbinolamide derivatives with the outcome being a better understanding of their potential roles in bioactive compounds. A second area of interest is in the rates of enolate production as a function of ring-strain and antiaromaticity. A focus of these studies is to provide a better understanding of how enzymes are capable of so effectively catalyzing enolate formation relative to chemical catalysts.