My group pursues new strategies that address the challenge of chemical synthesis in the face of growing concerns over fossil fuel utilization. By developing novel synthetic organic and organometallic methodologies, we focus on the design of chemical transformations that efficiently convert renewable starting materials into chemicals of functional importance. This program encompasses both target oriented and methods based synthetic approaches, and applies high standards of atom- and step- economies to enable sustainable chemical synthesis. My group works in a collaborative, multi-disciplinary setting on problems ranging from complex molecule synthesis to bulk chemical production. Correspondingly, students develop a broad range of problem solving techniques that require expertise in modern synthetic organic and analytical techniques.
Natural Products Total Synthesis
Natural products are powerful tools with which to explore a wide variety of biological phenomena. In my group, target selection and synthetic design focus on biomimetic approaches to natural products, which then provide platforms from which to further explore molecular function and biological origin. Initial efforts are targeting lignan natural products, where total synthesis will serve as a springboard to address current challenges in plant cell wall biosynthesis and plant defense.
Feedstock Chemicals from Renewable Resources
In order for the burgeoning bio-fuels industry to compete with current petrochemical manufacturing, waste streams that are created during bio-mass refinement must be converted into value-added chemicals. My group is investigating new catalytic processes that convert current bio-refining “waste” into important commodity chemicals. Initial efforts are focusing on the development of novel, well-defined transition metal complexes to effect chemo- and regioselective dehydration and deoxygenation reactions of polyoxygenated substrates.
(5) An Atom-Economic Synthesis of Nitrogen Heterocycles from Alkynes. Trost, B. M.; Lumb, J.P.; Azzarelli, J. M. J. Am. Chem. Soc. 2011, 133, 740.
(4) ortho-Quinone Methides from para-Quinones: Total Synthesis of Rubioncolin B. Lumb, J.P.; Choong, K. C.; Trauner, D. J. Am. Chem. Soc. 2008, 130, 9230.
(3) Biomimetic Synthesis of the IDO Inhibitors Exiguamine A and B. Volgraf, M.; Lumb, J.P.; Brastianos, H. C.; Carr, G.; Chung, M. K. W.; Munzel, M.; Mauk, A. G.; Andersen, R. J.; Trauner, D. Nature Chemical Biology, 2008, 4, 535.
(2) Pericyclic Reactions of Prenylated Naphthoquinones: Biomimetic Synthesis of Mollugin and Microphyllaquinone. Lumb, J.P.; Trauner, D. Org. Lett. 2005, 7, 5865.
(1) Biomimetic Synthesis and Structure Elucidation of Rubicordifolin, a Cytotoxic Natural Product from Rubia cordifolia. Lumb, J.P.; Trauner, D. J. Am. Chem. Soc. 2005, 127, 2870.
CHEM-211W Organic Chemistry 1 Lectures
CHEM-212W Introductory Organic Chemistry 1
CHEM-572 Synthetic Organic Chemistry
CHEM-629 Organic Synthesis