Development of a research based laboratory course in natural products chemistry

CHED 1502

Thomas A. Newton, newton@maine.edu, Department of Chemistry, University of Southern Maine, P.O. Box 9300, 96 Falmouth St, Portland, ME 04104 and Beth Hill, beth.hill@maine.edu, Department of Applied Medical Sciences, University of Southern Maine, P.O. Box 9300, Portland, ME 04104-9300.
This talk will describe a general strategy for developing research-based laboratory curricula. Essential components for this approach, e.g. combinatorial chemistry, will be illustrated with a specific example: Panduratin A, first isolated from the rhizomes of Boesenbergia pandurata in 1982, has been shown to cause apoptosis in human cancer cells. The biological activity of this compound, the availability of rhizomes of other members of the ginger family, and a 2-step synthesis of structural analogs (Figure 1) led us to create a research-based laboratory course that demonstrates the interdisciplinary nature of natural products chemistry. Students develop skills including searching the chemical literature, extracting plant materials, chromatography, synthesis, structure elucidation, biological testing and the development of structure activity relationships. The features of this approach that make original research feasible in an undergraduate laboratory course will be discussed. Figure 1-A generalized 2-step synthesis of panduratin A and structural analogs. In panduratin A R1 represents OH groups at positions 2 and 6 and an OCH3 group at position 4 of the aromatic ring; R2 = H; R3 = CH=C(CH3)2.