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Florida Gulf Coast University

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Chemistry (B.A.)

Daniel Paull

Assistant Professor, Chemistry
Phone: (239) 745-4335
E-Mail: dpaull@fgcu.edu
Office: LIB 461C

Education

  • Postdoctoral Fellow, Organic Synthesis, The University of Texas at Austin, 2009-2013
  • Doctor of Philosophy, Organic Chemistry, Johns Hopkins University, 2009
  • Master of Arts, Chemistry, Johns Hopkins University, 2006
  • Bachelor of Science, Chemistry, ACS Certified, Rhodes College, 2003

Research Interests

In the Paull labs, our main goal is the development of new asymmetric chemical methods in organic synthesis, and the use of these methods to produce compounds of biological interest. We have several projects with ongoing efforts toward pharmacophores (e.g. chloro- and fluoro-hydrins, lactams, and furans), biomolecules (e.g. terpenes, amino acids), natural product analogues (e.g. based on bromophycolide, resveratrol, isocymobarbatol) and pharmaceutics (SSRIs, cancer and osteoporosis targets). While the synthesis of these new biologics is of utmost importance, the creation of novel synthetic methodology to get there also provides highly useful technology to many thousands of labs around the globe to allow them to make new compounds for their specific uses. To this end, we have several ongoing method development initiatives of broad potential impact to explore new areas of chemical synthesis. These areas are divergent yet synergistic, and each has many potential individual methods of broad utility, targeting many potential biologically important compounds. Our relatively short synthetic sequences will be carried out with an eye towards making simple derivatization easy for broad chemical biology testing and future clinical candidates. Together, these methods will provide rapid access to a great many biomolecules and potential drugs.

A central effort in our labs revolves around emerging high-valent palladium catalysis. Palladium is fast becoming one of the most versatile metals for organic synthesis, and we are developing new uses for this amazing catalyst. Specifically, we are interested in the ability of chiral Pd complexes (and those of similar metals Ni, Pt, and Au) to activate olefins (C=C p-bonds) toward reaction with nucleophiles of various types, including p-donors, halogens, and O- and N-compounds. These reactions mimic certain biological processes and attempt to become as efficient in rapid functionalization as possible, using only 0.1–1 mol% relative to the reagents while creating several stereocenters simultaneously.

Another initiative is the development new chemical methods that bridge the gap between difficult industrial reactions and green laboratory synthesis by utilizing novel solid-phase (SP) catalytic variations of well-known industrial processes. We are designing SP catalysts that have the potential to perform difficult synthetic reactions under normal laboratory conditions with easily recoverable, reusable solid-supported metallic catalysts. These green processes have the potential to positively impact many industrial processes, as well as many thousands of small laboratories endeavoring to make simple organics for biological testing (including ours!). Lastly, we are also designing new organocatalytic methods for alpha-functionalization of carbonyl derivatives. This project addresses missing links in organocatalysis and attempts to fill those gaps with useful, simple methods by altering known organotechnology to work in new areas.

Collaborators

  • Prof. Arsalan Mirjafari (FGCU Department of Chemistry and Physics); solid-phase catalysis
  • Prof. Lyndsay Rhodes (FGCU Department of Biological Sciences); targets for treatment of osteoporosis and other areas of bone health, diet, and obesity
  • Prof. Gregory Boyce (FGCU Department of Chemistry and Physics); organocatalytic reactions

Selected Publications(from 18 total; citations as of Feb 2015)

Primary Research:

  • Paull, D. H.; Fang, C.; Donald, J. R.; Pansick, A.; Martin, S. F. “Bifunctional Catalyst Promotes Highly Enantioselective Bromolactonizations to Generate Stereogenic C–Br Bonds” J. Am. Chem. Soc. 2012, 134(27), 11128–11131. (Citations: 60) Linked
  • Paull, D. H.; Scerba, M. T.; Alden-Danforth, E.; Widger, L. R.; Lectka, T. “Catalytic, Asymmetric a-Fluorination of Acid Chlorides: Dual Metal–Ketene Enolate Activation” J. Am. Chem. Soc. 2008, 130(51), 17260–17261. (Citations: 56) Linked
  • Paull, D. H.; Alden-Danforth, E.; Wolfer, J.; Dogo-Isonagie, C.; Abraham, C. J.; Lectka, T. “An Asymmetric, Bifunctional Catalytic Approach to Non-Natural a-Amino Acid Derivatives” J. Org. Chem. 2007, 72(14), 5380–5382. (Citations: 23) Linked
  • Halden, R. U.; Paull, D. H. “Co-Occurrence of Triclocarban and Triclosan in U.S. Water Resources” Environ. Sci. Technol. 2005, 39(6), 1420–1426. (Citations: 225) Linked

Reviews Articles:

  • Paull, D. H.; Weatherwax, A.; Lectka, T. “Catalytic, Asymmetric Reactions of Ketenes and Ketene Enolates” Tetrahedron 2009, 65(34), 6771–6803. (Citations: 77) Linked
  • Paull, D. H.; Abraham, C. J.; Scerba, M. T.; Alden-Danforth, E.; Lectka, T. “Bifunctional Asymmetric Catalysis: Cooperative Lewis Acid/Base Systems” Acc. Chem. Res. 2008, 41(5), 655–663. (Citations: 190) Linked

Selected Presentations

  • “Vicinal Difunctionalization of C=C Double Bonds.” Talk given at: (a) ACS Conference, Aug 2013; (b) FGCU, Jan 2014; (c) Coker College, Jan 2014; (d) Manhattan College, Feb 2014
  • “Enantioselective, Bifunctional Catalysis of Halolactonizations, and the Formal Total Synthesis of Stemofoline.” Talk given at The Lieber Institute of JHMI, June 7, 2013.
  • “Bifunctional Asymmetric Catalysis of Ketene Reactions; Methodology and Target Synthesis.” Talk given at: (a) MIT, 4/6/2009; (b) UT-Austin, 4/17/2009; (c) JHU, 6/17/2009.
  • “Resveratrol: Discovering the Miracle-Drug Antioxidant of Red Wine.” Talk given at: (a) Johns Hopkins University, November 12, 2008; (b) The University of Texas at Austin, 9/6/2011.

Current Funding

  • NIH Equipment Utilization Project, $45,000, beginning 2014

Past Funding

  • NIH Postdoctoral Fellowship, $107,000 (F32-GM31077), 24 mo. 2011 - 2012
  • Eugene W. and Susan C. Zeltmann Fellowship, $66,000, 12 mo. 2008 – 2009

Full Curriculum Vitae