Guest Speaker: Levi Stanley - Iowa State University
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105
Dr. Levi Stanley of Iowa State University will present his work:
Over 45% of the top 200 pharmaceutical compounds (by US retail sales in 2012) are small molecule heterocycles. These heterocycles are currently used to treat human disease ranging from cancer to diabetes to microbial infections. The prevalence of heterocycles as medicinally important compounds continues to drive research into strategies to from new heterocyclic scaffolds and methods that streamline the syntheses of complex heterocycles.
The focus of synthetic chemists is increasingly shifting toward the identification and development of catalysts that establish new reactivity patterns, enable the formation of new molecular architectures, and improve the efficiency of synthetic routes. However, the development of new catalysts and synthetic methods is often performed with simple molecules containing minimal functionality. Straightforward transfer of these catalytic methods to the synthesis and functionalization of heterocycles remains challenging and understudied.
My research group seeks to develop catalytic transformations that rapidly build complexity into the structure of bioactive heterocycles, primarily polycyclic indole derivatives. To date, we have identified palladium catalysts that promote regioselective prenylations of indoles, rhodium catalysts that promote enantioselective hydroacylations (additions of aldehydes across alkenes) of N-vinylindole and N-allylindoles, and magnesium and copper catalysts that promote enantioselective 1,3-dipolar cycloadditions to form indole derivatives. The development of these synthetic methods and their applications in the synthesis of bioactive heterocycles will be the focus of this seminar.