Wednesday, October 2, 2013 — 2:30 PM EDT
Functionalization of Indoles: Applications to the Total Synthesis of Natural Products
Dr. Michael Kerr
Department of Chemistry
Wednesday, October 2, 2013
C2-361 (Reading Room)
Abstract: We have developed methods for the efficient functionalization of the indole moiety at either the 3- or 2-posiiton using carbenoids or radicals derived from 1,3-dicarbonyl species.1 Recent progress in methods development will be discussed as well as the application of these methods to the synthesis of natural products both completed2 and in progress.
1.  a) Johansen, M.B.; Kerr, M.A. Direct Functionalization of Indoles: Copper-Catalyzed Malonyl Carbenoid Insertions. Org. Lett. 2010, 12, 4956. b) Magolan, J.; Kerr, M.A. Expanding the Scope of Mn(OAc)3-Mediated Cyclizations: Synthesis of the Tetracyclic Core of Tronocarpine. Org. Lett. 2006, 8, 4561. c) Gibe, R.; Kerr, M.A. Convenient preparation of indolyl malonates via carbenoid insertion. J. Org. Chem. 2002, 67, 6247-6249.
2. Magolan, J; Carson, C.A.; Kerr, M.A. Total synthesis of (+/-)-mersicarpine. Org. Lett., 2008, 10 1437.