Our research is directed toward solving puzzles. We want to learn the “why and how” of interesting and useful organic reactions. We are also interested in finding new synthetic methodology that will have utility in the synthesis of medicinally active and/or novel compounds. One of the central themes in our work is the use of light as a reagent.

In our work with alkenyl-substituted aromatic compounds, we have found a high degree of regio- and stereoselectivity using intramolecular photocycloadditions. This is a powerful tool in synthetic chemistry since carbon-carbon bond forming reactions that occur with selectivity are critical in the synthesis of complex molecules. One of the recent applications is formation of the polycyclic compound shown in Scheme 1. This tetracyclic compound was made from a silylated phenol. Students working on this project have performed organic synthesis and learned to solve difficult spectroscopic puzzles.

Scheme 1. Novel compound synthesis

Our efforts are also directed toward understanding the mechanism for selectivity in intermolecular photocycloadditions. Temperature studies of the cycloaddition between styrene and benzaldehyde have indicated that pi-stacking plays a role in the stereoselectivity of the reaction. Solving this puzzle may lead to the exploitation of the photocycloaddition in the synthesis of important four-member ring structures such as the anti-viral compound oxetanocin as shown in Scheme 2.

Scheme 2. Biologically active target for photochemical synthesis

We have an interest in the process of photoaffinity labeling. This procedure provides information about the site of binding for substrate-enzyme complexes. One of the puzzles that we have recently solved pertains to the photochemical cleavage of the benzyl-sulfur bond. We are currently investigating the generality of this procedure and we want to find applications where substrates can be modified with the benzylthio group. Irradiation of those modified substrates when they are in the binding site will allow analysis of the substrate-enzyme interaction.

We have been involved in a number of collaborations in the past and we are continuing to work with other chemists. We studied synthetic modification of the COX-II inhibitor diclofenac (a non-steroidal anti-inflammatory drug) in a project with Prof. Dan Simmons. We studied new methods for drug delivery in collaboration with Prof. Bill Pitt, a BYU chemical engineer. In collaboration with Prof. Morris Robins, we explored the photochemical behavior of substituted nucleosides which initiated our work in the field of photoaffinity labeling. Working with Prof. Delbert Eatough, we have explored mechanisms for photo-oxidation of nitrogen-containing organic compounds found in the atmosphere. In conjunction with Prof. Matt Linford we have performed calculations on silyl radical species formed on silicon surfaces generated in the presence of various organic liquids. With Prof. Ty Redd of Southern Utah University, we have studied and reported on the asymmetric dihydroxylation of allenes. This is new synthetic methodology for the enantioselective formation of -hydroxy ketones. In a joint effort with Prof. Paul Savage, we have developed new software designed to aid in the student’s ability to learn organic chemistry. This software is called Organic Reaction Animations (ORA). We are collaborating with Prof. Gregor Fels from the University of Paderborn in Germany on a related project that deals with the design of a web-based organic reaction animating tool.

The students in our group obtain a solid understanding and expertise in synthetic and physical organic chemistry. We also gain exposure to biochemistry, inorganic synthesis, kinetics, computational chemistry, and analytical techniques.