ORGANIC
LETTERS
2011
Vol. 13, No. 10
2726–2729
Ruthenium-Catalyzed γ-Carbolinium Ion
Formation from Aryl Azides; Synthesis of
Dimebolin
Huijun Dong, Regina T. Latka, and Tom G. Driver*
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street,
Chicago, Illinois 60607-7061, United States
Received March 29, 2011
ABSTRACT
A range of γ-carbolines were produced stereoselectively from ruthenium(III)-catalyzed reactions of 3-pyridyl substituted aryl azides. Other
catalysts and conditions were neither as selective nor as high-yielding. This method was used to synthesize dimebolin in a concise and efficient
manner.
The synthesis of N-heterocycles through the formation
of CÀN bonds from CÀH bonds improves the synthetic
efficiency of the synthesis of these medicinally important
molecules by eliminating functional group manipu-
lation.1,2 β-3À5 and γ-carbolines6 are particularly attractive
targets for the development of CÀH bond functionali-
zation methods because they constitute the core of
many biologically active compounds.7 Dimebolin (aka
latrepiridine)8 is a γ-tetrahydrocarboline that was under
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10.1021/ol2008268
Published on Web 04/25/2011
2011 American Chemical Society