- Council on Science and Technology Postdoctoral Fellow (2007-2010), Princeton University (Erik J. Sorensen)
- Ph.D. (2007), University of Minnesota (Thomas R. Hoye)
- B.S. (2002), Carroll College
Synthesis Research Interests
Research in the Jeffrey laboratory is focused on addressing important, unmet challenges in target directed synthesis. Areas of research are identified using a synergistic approach where (1) inspiration from structurally and biologically interesting molecular targets drives reaction discovery, and (2) innovation in methodology enables new strategies for target-directed synthesis.
Some areas of research in our laboratory are focused on the development of new methods/strategies to generate and control electrophilic nitrogen species that will enable the direct functionalization of alkenes and C-H bonds-the two most ubiquitous functional groups in organic molecules. These research interests are focused on the development of: (i) new heterocycloaddition reactions, (ii) a concise and general synthesis of a family of biologically active alkaloids, and (iii) new methods of metal-mediated amination.
Ecology, Evolution and Conservation Biology Research Interests
Chemical Ecology, Plant-Animal Interactions, Physiological Ecology, Global Change
Secondary metabolism in plants and other organisms plays an extremely important role in reproduction, defense and growth. Chemical-Ecology as a field has made remarkable advances related to uncovering the role of these metabolites in the ecological interactions between species. Despite these major advances, studies in chemical-ecology have largely focused on understanding the role of natural products in isolated interactions between organisms (e.g. single plant-insect and insect-insect interactions). While these studies have highlighted important role of natural products in ecology, major questions related to the evolution and impact of these molecules on ecological interactions have not been comprehensively addressed. We have begun to address a few long-standing questions ecology through the initiation of a comprehensive phytochemical study of the Genus Piper, a tropical shrub with a broad diversity of both natural products and species. It is our primary goal to address the Genus-wide role of phytochemistry in the tri-trophic interaction of Piper, a specialist caterpillar, and the caterpillar’s primary predator (a parasitic wasp). Previous studies have uncovered that natural products produced by Piper have a strong role by increasing the susceptibility of the caterpillar to parasitism via immune system suppression. The specific aims of our group seek to: (1) map the diversity of secondary metabolism to the diversity of Eois caterpillars, (2) explore the link between phytochemical variation and the speciation of the caterpillar, and (3) understand the role of mixtures of natural products in the overall biologically activity of defensive compounds. These studies have stimulated the development of new approaches to metabolic characterization of phytochemically diverse species, led to the discovery of new natural products, and to the development of syntheses of some of these natural products.
- Barnes, K.L.; Chen, K.; Catalano, V.J.; Jeffrey, C.S. New building blocks for iminosugars: a concise synthesis of polyhydroxylated N-alkoxypiperidines through an intramolecular azepine ring contraction. Org. Chem. Front. 2015, 2, 497-501.
- Anumandla, D.; Littlefield, R.; Jeffrey, C.S. Oxidative 1,4-Diamination of Dienes Using Simple Urea Derivatives. Org. Lett. 2014, 16, 5112-5115.
- Song, M.; Delaplain, P.; Nguyen, T.T.; Liu, X.; Wickenberg, L.; Jeffrey, C.; Blomquist, G.J.; Tittiger, C. exo-Brevicomin biosynthetic pathway enzymes from the Mountain Pine Beetle, Dendroctonus ponderosae. Insect Biochem. Mol. Biol. 2014, 53, 73-80.
- Barnes, K.L.; Koster, A.K.; Jeffrey, C.S. Trapping the elusive aza-oxyallylic cation: new opportunities in heterocycloaddition chemistry. Tetrahedron Lett. 2014, 55, 4690-4696.
- Gaia, A.M.; Yamaguchi, L.F.; Jeffrey, C.S.; Kato, M.J. Age-dependent changes from allylphenol to prenylated benzoic acid production in Piper gaudichaudianum Kunth. Phytochemistry (Elsevier) 2014, 106, 86-93.
- Song, M.; Gorzalski, A.; Nguyen, T.T.; Liu, X.; Jeffrey, C.; Blomquist, G.J.; Tittiger, C. exo-Brevicomin Biosynthesis in the Fat Body of the Mountain Pine Beetle, Dendroctonus ponderosae. J. Chem. Ecol. 2014, 40, 181-189.
- Jeffrey, C.S.; Leonard, M.D.; Glassmire, A.E.; Dodson, C.D.; Richards, L.A.; Kato, M.J.; Dyer, L.A. Antiherbivore prenylated benzoic acid derivatives from Piper kelleyi. J. Nat. Prod. 2014, 77, 148-153.
- Freitas, G.C.; Batista, J.M.; Franchi, G.C.; Nowill, A.E.; Yamaguchi, L.F.; Vilcachagua, J.D.; Favaro, D.C.; Furlan, M.; Guimaraes, E.F.; Jeffrey, C.S.; Kato, M.J. Cytotoxic non-aromatic B-ring flavanones from Piper carniconnectivum C. DC. Phytochemistry (Elsevier) 2014, 97, 81-87.
- Whitehead, S.R.; Jeffrey, C.S.; Leonard, M.D.; Dodson, C.D.; Dyer, L.A.; Bowers, M.D. Patterns of Secondary Metabolite Allocation to Fruits and Seeds in Piper reticulatum. J. Chem. Ecol. 2013, 39, 1373-1384.
- Acharya, A.; Eickhoff, J.A.; Jeffrey, C.S. Intramolecular aza-[4 + 3] cycloaddition reactions of α-halohydroxamates. Synthesis 2013, 45, 1825-1836.
- Jeffrey, C.S.; Anumandla, D.; Carson, C.R. 1,4-Diamination of Cyclic Dienes via a (4 + 3) Cycloaddition of Diaza-allyl Cationic Intermediates. Org. Lett. 2012, 14, 5764-5767.
- Jeffrey, C. S.; Barnes, K. L.; Eickhoff, J. A.; Carson, C. R. Generation and Reactivity of Aza-Oxyallyl Cationic Intermediates: Aza-[4 + 3] Cycloaddition Reactions for Heterocycle Synthesis. J. Am. Chem. Soc. 2011, 133, 7688-7691.
- Hoye, T.R.; Jeffrey, C.S.; Nelson, D.P. Dynamic Kinetic Resolution During a Vinylogous Payne Rearrangement: A Concise Synthesis of the Polar Pharmacophoric Subunit of (+)-Scyphostatin. Org. Lett. 2010, 12, 52-55.
- Frie, J.L.; Jeffrey, C.S.; Sorensen, E.J. A Hypervalent Iodine-Induced Double Annulation Enables a Concise Synthesis of the Pentacyclic Core Structure of the Cortistatins. Org. Lett. 2009, 11, 5394-5397.
- Hoye, T.R.; Jeffrey, C.S.; Shao, F. Mosher Ester Analysis for the Determination of Absolute Configuration of Stereogenic (a.k.a. Chiral) Carbinol Carbons. Nat. Protoc. 2007, 2, 2451-2458.
- Hoye, T.R.; Dvornikovs, V.; Fine, J.M.; Anderson, K.R.; Jeffrey, C.S.; Muddiman, D.C.; Shao, F.; Sorensen, P.W.; Wang, J. The Structure Determination of the Sulfated Steroids PSDS and PADS - New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone. J. Org. Chem. 2007, 72, 7544-7550.
- Hoye, T.R.; Jeffrey, C.S. Student Empowerment through 'Mini-Microscale' Reactions: The Epoxidation of 1.0 mg of Geraniol. J. Chem. Educ. 2006, 83, 919-920.
- Sorensen, P.W.; Fine, J.M.; Dvornikovs, V.; Jeffrey, C.S.; Shao, F.; Wang, J.; Vrieze, L.A.; Anderson, K.R.; Hoye, T.R. Mixture of New Sulfated Steroids Functions as a Migratory Pheromone in the Sea Lamprey. Nature Chem. Biol. 2005, 1, 324-328.
- Hoye, T.R.; Jeffrey, C.S.; Tennakoon, M.A.; Wang, J.; Zhao, H. Relay Ring-Closing Metathesis (RRCM): A Strategy for Directing Metal Movement Throughout Olefin Metathesis Sequences. J. Am. Chem. Soc. 2004, 126, 10210-10211.