Biosciences Graduate Program

Gregory K. Friestad, BS, PhD

Portrait

Associate Professor of Chemistry

Contact Information

Office: E455 CB
Iowa City, IA 52242
Office Phone: 319-335-364

Email: gregory-friestad@uiowa.edu
Web: More About Dr. Friestad - Related Websites and Resources

Education

BS, Chemistry, Bradley University
PhD, Organic Chemistry, University of Oregon

Post Doctoral, Organic Synthesis, University of Pennsylvania

Education/Training Program Affiliations

Biosciences Graduate Program

Research Summary

Organic synthesis is crucial to biomedical research and nanotechnology because organic chemists design and provide new substances with the improved properties needed to achieve the amazing advances we see in these areas. Fundamental basic research in organic chemistry allows us to make new substances more efficiently, and with less environmental impact. Researchers in the Friestad Group address problems in synthetic methodology and natural product synthesis, with special emphasis on efficiency by developing useful carbon-carbon bond constructions. Our primary synthetic targets are biologically active substances which have significant potential either as biological probes in health sciences research or as lead compounds for development of new disease therapies. Students develop new synthetic methods and apply them to natural product targets, routinely using research instrumentation such as nuclear magnetic resonance (NMR) and high-performance liquid chromatography (HPLC). Such projects, combining the depth of methodology research with the breadth of total synthesis training, are outstanding preparation for industrial or academic research. Friestad Group alumni have careers in pharmaceutical companies both big and small, as well as teaching and research positions in academia. Specific projects we have developed involve reaction methodology at the interface with organometallic chemistry, ranging from organosilicon and organotransition metal chemistry to free radical reactions. We've developed silicon-tethered diastereoselective radical cyclizations leading to amino alcohols. We've designed and implemented a novel chiral N-acylhydrazone motif for asymmetric addition reactions which provides for excellent enantioselectivity from chiral auxiliaries or catalysts. Our chiral N-acylhydrazones have proved to be broadly useful acceptors for additions of alkyl radicals and a wide range of nucleophiles including hydride and allylsilane reagents. We found that photolysis of Mn2(CO)10 enables radical addition to chiral N-acylhydrazones using a broad range of precursors, including primary alkyl halides and multifunctional compounds. This method is now in use for synthesis of complex natural product targets.

Date Last Modified: 06/07/2014 - 21:56:23