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Sidney Malik Wilkerson-Hill - University of North Carolina, Chapel Hill

Host: Beth Elacqua

"Orphaned Cyclopropanes"

Abstract: The goal of the Hill group is to develop new reactions to obtain pyrethroids, small molecules used to combat vectors for malaria (e.g., Anopheles gambiae). We are particularly interested in identifying new small molecule pyrethroids with enhanced photostability, reduced off target toxicological properties to beneficial pollinators, and reduced insect resistance profiles. To accomplish these goals, my research group is developing new routes to orphaned cyclopropanes, a structural motif found in all pyrethroids, by using 1) biomimicry and frustrated Lewis acid-base pairs (FLP’s), 2) reagent-based approaches toward natural product families; and 3) chemotype-centric approaches using sulfones as non-stabilized carbene equivalents. These methods to obtain orphaned cyclopropanes also enable the discovery of new cyclopropane-containing medicines, since they permit rational structure activity relationship studies at the 1,1-dialkyl position - a traditionally understudied portion of chemical space.