Department of Chemistry
C2 280
200 University Ave. W
Waterloo, Ontario,
Canada N2L 3G1
Phone: (519) 888-4567 ext 32129
Fax: (519) 746-0435
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
Western University
Wednesday, October 2, 2013
2:30 p.m.
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. [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.