个人简介

B.S., Bradley University (1990) Ph.D., University of Oregon (1995) NIH Postdoctoral Fellowship, University of Pennsylvania (1995-1998) Visiting Professor and JSPS Fellowship, Kobe Pharmaceutical University (2003) Visiting Professor, University of Wisconsin-Madison (2005)

研究领域

Organic Chemistry

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.

近期论文

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Friestad, G. K.; Sreenilayam, G.; Cannistra, J. C.; Slominski, L. M. "Preparation of Enol Ester Epoxides and Their Ring-Opening to alpha-Silyloxyaldehydes." Tetrahedron Lett. 2012, 53, 5064-5067. Friestad, G. K.; Ji, A.; Baltrusaitis, J.; Korapala, C. S.; Qin, J. "Scope of Stereoselective Mn-Mediated Radical Addition to Chiral Hydrazones and Application in a Formal Synthesis of Quinine." J. Org. Chem. 2012, 77, 3159-3180. Friestad, G. K. "Asymmetric Radical Addition to Chiral Hydrazones." In Topics In Current Chemistry: Radicals in Synthesis III; Gansauer A.; Heinrich, M., Eds., Springer-Verlag: Berlin, 2012, vol. 320, pp. 61-92. Friestad, G. K. "Organomanganese-Mediated Radical Reactions." In The Chemistry of Organo-Manganese Compounds; Marek, I.; Rappoport, Z., Eds.; Wiley: Chichester, United Kingdom, 2011, pp. 559-584. Friestad, G. K.; Ji, A.; Korapala, C. S.; Qin, J. "Intermolecular Radical Addition to N-Acylhydrazones as a Stereocontrol Strategy for Alkaloid Synthesis: Formal Synthesis of Quinine." Org. Biomol. Chem. 2011, 4039-4043. Friestad, G. K.; Sreenilayam, G. "1,5-Polyols: Challenging Motifs for Configurational Assignment and Synthesis." Pure Appl. Chem. 2011, 83, 461-478. Friestad, G. K.; Sreenilayam, G. "Versatile Configuration-Encoded Strategy for Rapid Synthesis of 1,5-Polyol Stereoisomers." Org. Lett. 2010, 12, 5016-5019. Friestad, G. K. "Asymmetric Methods for Radical Addition to Imino Compounds." In Chiral Amine Synthesis. Methods, Developments and Applications; Nugent, T., Ed.; Wiley-VCH: Weinheim, Germany, 2010; pp. 51-74. Friestad, G. K.; Lee, H. J. "Trans-2,5-Disubstituted Tetrahydrofurans via Additions of Carbon Nucleophiles to the Strained Bicyclic Acetal 2,7-Dioxabicyclo[2.2.1]heptane." Org. Lett. 2009, 11, 3958-3961. Friestad, G. K.; Banerjee, K. "Synthesis of gamma-Amino Esters via Mn-Mediated Radical Addition to Chiral gamma-Hydrazonoesters." Org. Lett. 2009, 11, 1095-1098. Friestad, G. K.; Wu, Y. "Intermolecular Non-Reductive Alkylation of Enamides via Radical-Polar Crossover." Org. Lett. 2009, 11, 819-822. Friestad, G. K. "Reaction of Acetals with Organometallic Reagents." in Science of Synthesis, Vol. 40a: Compounds with One Saturated Carbon-Heteroatom Bond: Amines and Ammonium Salts, Enders, D.; Shaumann, E., Eds.; Thieme: Stuttgart, Germany, 2009, pp. 91-110. Friestad, G. K. "Addition of Carbanions to Azomethines." in Science of Synthesis, Vol. 40a: Compounds with One Saturated Carbon-Heteroatom Bond: Amines and Ammonium Salts, Enders, D.; Shaumann, E., Eds.; Thieme: Stuttgart, Germany, 2009, pp 305-342. Friestad, G. K.; Jiang, T.; Fioroni, G. M. "Stereocontrol in Radical Mannich Equivalents for Aminosugar Synthesis: Haloacetal and 2-(Phenylthio)vinyl Tethered Radical Additions to alpha-Hydroxyhydrazones." Tetrahedron 2008, 64, 11549-11557. Friestad, G. K.; Ji, A. "Mn-Mediated Coupling of Alkyl Iodides and Ketimines: A Radical Addition Route to alpha,alpha-Disubstituted alpha-Aminoesters" Org. Lett. 2008, 10, 2311-2313. Korapala, C. S.; Qin, J.; Friestad, G. K. "Quinine Synthesis Studies: A Radical-Ionic Annulation via Mn-Mediated Addition to Chiral N-Acylhydrazones" Org. Lett. 2007, 9, 4243-4246. Friestad, G. K.; Mathies, A. K. "Effects of alpha-Alkoxy Substitution and Conformational Constraints on 6-exo Radical Cyclizations of Hydrazones via Reversible Thiyl and Stannyl Additions." Tetrahedron 2007, 63, 9373-9381. Friestad, G. K.; Jiang, T.; Mathies, A. K. "Enhanced Reactivity in Radical Cyclizations of Hydrazones Using the Silicon-Tethered 1-Bromovinyl Group." Tetrahedron 2007, 63, 3964-3972. Friestad, G. K.; Jiang, T.; Mathies, A. K. "Aldehyde-Selective Wacker Oxidation in a Thiyl-Mediated Vinyl Group Transfer Route to Daunosamine." Org. Lett. 2007, 9, 777-780. Friestad, G. K.; Mathies, A. K. "Recent Developments in Asymmetric Catalytic Addition to C=N Bonds." Tetrahedron 2007, 63, 2541-2569.