Julie Pigza

Assistant Professor

Organic Chemistry

julie.pigza@usm.edu

Education:

Experience:

  • Assistant Professor of Chemistry, Queensborough Community College/CUNY (2010-2013)
    QCC Chemistry Department
  • Postdoctoral research associate; University of California San Diego (2008-2009)
    Advisor: Dr. Ted Molinski
    UCSD Chemistry Department
    Marine natural products isolation and characterization; non-natural amino acid synthesis

Research Interests:

Research in my group will focus on methodology development and the total synthesis of natural products. One area that we are 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 onto a substrate and offer an extension to using allyl silane. We are currently in the process of making a variety of protected oxyallyl silanes with ester, ether, carbonate, and silyl groups. My research group is also interested in alkaloid natural products containing a piperidine ring. Alkaloids are structurally complex and have interesting biological properties. We would like to develop the synthesis of piperidine-containing target backbones within larger alkaloid natural products. Previously, I worked on the total synthesis of the Lycopodium alkaloid, serratezomine A, as part of my graduate work and my research interests stem from this experience. My postdoctoral work provided me with background in natural production isolation and structure elucidation and is also an area of interest to pursue in conjunction with local area high school students. Lastly, 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 research group will learn a variety of synthetic organic methods and purification techniques as well as analytical methods including NMR (both 1D and 2D pulse sequences), IR, and mass spectrometry.

Honors and Awards:

  • Visiting Scholar Appointment through Vanderbilt University through my graduate advisor, Dr. Jeffrey Johnston (2010-2013)
  • Acknowledged for insightful contributions in a publication (Flores, B.; Molinski, T. F. Org. Lett. 2011, 13, 3932-3935)
  • Pfizer Diversity in Organic Chemistry Graduate Fellowship (Indiana University), 2005-2006
  • Jack K. Crandall Award in Organic Chemistry (Indiana University), 2004
  • Eli Lilly Organic Chemistry Fellowship (Indiana University), 2002
  • Oak Ridge National Laboratory Summer Internship Award (Allegheny College), 2001
  • ACS Polymer Education Award for Excellence in Organic Chemistry (Allegheny College), 2000

Professional Membership and Service:

  • American Chemical Society
  • Phi Beta Kappa (Eta Chapter, PA)
  • The National Scholars Honor Society
  • Reviewer: Organic Letters, ACS Petroleum Research Fund grant, book chapter for McGraw Hill
  • Moderator: 244th National ACS Meeting, New Reactions and Methodology Session (Philadelphia, PA)
  • Demonstrator at the National Chemistry Week at the New York Hall of Science
  • Judge at the WAC Lighting Foundation Invitational High School Science Fair

Publications:

  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. (Note: made the top most read articles in J. Org. Chem. during the Jan-Mar 2013 quarter).
  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.

Grants:

  • Eppley Foundation Grant entitled “A Mechanistic Study of the Conversion of Esters to Ethers: Seeking a Tunable Protocol that Applies to both Aromatic and non-Aromatic Esters”, award number GR04988, amount $21,877, May 1, 2014 – June 1, 2015.
  • PSC-CUNY 44 Traditional B Award entitled “Acquisition of a Solvent Rotary Evaporation System for Undergraduate Organic Chemistry Research”, award number 66267-00 44, amount $2273.00, July 1, 2013 – August 31, 2013.
  • American Chemical Society Petroleum Research Fund grant (ACS-PRF) entitled “Development of Oxyallyl Silanes as Homoenolate Equivalents in the Oxidative Addition to Vinylogous Amides”, PRF# 51776-UNI1, amount $50,000, January 1, 2012 – August 31, 2013.
  • PSC-CUNY 42 Traditional B Award entitled “Oxyallyl Silanes as Homoenolate Equivalents: Synthesis and Addition to Electrophiles”, award number 64642-00 42, amount $5057.26, July 1, 2011 – December 30, 2012.

Presentations:

  1. Julie A. Pigza, “Methodology Development using Oxyallyl Silanes as Homoenolate Equivalents”, seminar, 244th National ACS Meeting, August 21, 2012, Philadelphia, PA
  2. Julie A. Pigza, “Methodology Development using Oxyallyl Silanes as Homoenolate Equivalents”, seminar, Chemistry Department Seminar Series, February 24, 2012, QCC, Bayside, NY
  3. Julie A. Pigza, “Lessons Learned During the Total Synthesis of (+)-Serratezomine A”, seminar, Chemistry Departmental Meeting, December 8, 2010, Queensborough Community College, Bayside, NY
  4. Julie A. Pigza, Jeongseok Han, Daniel Mutnick, “Progress Toward the Total Synthesis of (+)-Serratezomine A”, presented at the following conferences:
    • Poster, 10th International Conference on the Chemistry of Antibiotics and Other Bioactive Compounds, August 12-15, 2007, Vanderbilt University, Nashville, TN
    • Seminar, Vanderbilt Institute of Chemical Biology Retreat, August 9, 2007, Vanderbilt University, Nashville, TN
    • Seminar, Pfizer Award Symposium in recognition of the graduate fellowship from the previous year, October 12-13, 2006, Pfizer, Groton, CT
    • Poster, Gordon Research Conference on Natural Products, July 23-28, 2006, Tilton School, Tilton, NH
    • Poster, Pfizer Award Symposium as a graduate fellowship recipient, September 29-30, 2005, Pfizer, Groton, CT
    • Poster, Eli Lilly Grantee Symposium as a graduate fellowship recipient, March 1-2, 2004, Eli Lilly, Indianapolis, IN
  5. Julie A. Pigza, “Structural Misassignments and Ambiguities in Natural Product Elucidation: A Focus on NMR as the Main Tool for Revision”, seminar, Chemistry Departmental Meeting, January 11, 2007, Vanderbilt University, Nashville, TN