Julie Pigza, Ph.D.

Assistant Professor, Department of Chemistry and Biochemistry

Research in my group will focus on methodology development and the total synthesis of natural products. One area that I am interested in is using oxyallyl silanes in synthetic methods. Oxyallyl silanes contain three orthogonal functional groups (vinyl, silyl, and hydroxyl) that can each be converted selectively depending on the reaction conditions. They provide a unique way to install three carbons and offer an extension to using allyl silane. I am interested in alkaloid natural products containing a piperidine ring. Alkaloids are structurally complex and have interesting biological properties. We would develop the synthesis of target backbones within these larger natural products. I am also excited to implement green chemistry techniques (see the 12 Principles of Green Chemistry on the ACS website) into standard organic reactions. Students in my group will learn a variety of organic synthesis techniques and purification as well as analytical methods including NMR, IR, and mass spectroscopy.

1. “Serratezomine A”, Pigza, J. A.; Johnston, J. N. Invited Book Chapter, Ch. 6 of “Total Synthesis of Natural Products. At the Frontiers of Organic Chemistry”, Li, J. J; Corey, E. J.; Springer-Verlag: Berlin, Heidelberg, March 5, 2013.

2. Pigza, J. A.; Han, J.-S.; Chandra, A.; Mutnick, D; Pink, M.; and Johnston, J. N. “Total Synthesis of the Lycopodium Alkaloid Serratezomine A Using Free Radical-Mediated Vinyl Amination to Prepare a β-Stannyl Enamine Linchpin” J. Org. Chem. (featured article) 2013, 78, 822-843.

3. Haines, N. R.; VanZanten, A. N.; Cuneo, A. A.; Miller, J. R.; Andrews, W. J.; Carlson, D. A.; Harrington, R. M.; Kiefer, A. M.; Mason, J. D.; Pigza, J. A.; Murphree, S. S. “A Sulfone-Based Strategy for the Preparation of 2,4-Disubstituted Furan Derivatives” J. Org. Chem. 2011, 76, 8131-8137.

4. “Benzenemethanamine, α-Phenyl- and Benzenemethanamine, α-Phenyl-Hydrochloride”, Pigza, J. A. Electronic Encyclopedia of Reagents for Organic Synthesis, Crich, D.; Charette, A. B.; Fuchs, P. L.; Molander, G. Eds.; John Wiley & Sons Ltd.: Sussex, 2011.

5. Pigza, J. A.; Molinski, T. F. “Diastereoselective Allylstannane Additions to (S)-5,6-Dihydro-2H-5-phenyloxazin-2-one. A Concise Synthesis of β-Methylisoleucine.” Org. Lett. 2010, 12, 1256-1259.

6. “Ketene”, Pigza, J. A. First Update, Electronic Encyclopedia of Reagents for Organic Synthesis, Crich, D.; Fuchs, P. L.; Molander, G.; Paquette, L. A. Eds.; John Wiley & Sons Ltd.: Sussex, 2009.

7. Pigza, J. A.; Quach, T.; Molinski, T. F. “Oxazoline-Oxazinone Oxidative Rearrangement. Divergent Syntheses of (2S,3S)-4,4,4-Trifluorovaline and (2S,4S)-5,5,5-Trifluoroleucine.” J. Org. Chem. 2009, 74, 5510-5515.

8. Chandra, A.; Pigza, J. A.; Han, J.-S.; Mutnick, D.; Johnston, J. N. “Total Synthesis of the Lycopodium Alkaloid (+)-Serratezomine A.” J. Am. Chem. Soc. 2009, 131, 3470-3471.

9. Shafer, C. M.; Pigza, J. A.; Molinski, T. F. “Allyl Silane Additions to Highly Electrophilic 5,6-Dihydro-2H-1,4-oxazinones.” Lett. Org. Chem. 2009, 6, 224-228.

10. “1-Methyl-2-Pyrrolidinone”, Pigza, J. A. First Update, Electronic Encyclopedia of Reagents for Organic Synthesis, Crich, D.; Fuchs, P. L.; Molander, G.; Paquette, L. A. Eds.; John Wiley & Sons Ltd.: Sussex, 2008.

11. “N-Iodosuccinimide”, Pigza, J. A. Second Update, Electronic Encyclopedia of Reagents for Organic Synthesis, Crich, D.; Fuchs, P. L.; Molander, G.; Paquette, L. A. Eds.; John Wiley & Sons Ltd.: Sussex, 2007.