Intramolecular cyclizations to [3,1,0] cyclohexanones from α-diazoketones and a non-hazardous synthesis of a diazoketone

ORGN 165

Matthew M. Bio1, Philip J. Pye1, Gary J. Javadi, gary_javadi@merck.com1, Z. Jake Song1, Mark Cameron1, Minetaka Isomura2, Marjorie See Waters, marjorie_waters@merck.com1, Juan J. Castano1, David L. Hughes3, and David M. Tschaen1. (1) Process Research, Merck & Co., Inc, PO Box 2000, Rahway, NJ 07065, (2) Department of Chemistry, University of Tokyo, (3) Department of Process Research, Merck & Co, Rahway, NJ 07065
A synthesis of an mGluR2/mGluR3 receptor agonist featuring a late stage photo-induced cyclopropanation will be presented along with the development of a high yielding, non explosive, and shelf stable replacement for diazomethane. Photo-induced cyclizations of this type are influenced by system electronics, solvent, and triplet sensitizer. Under optimized conditions, these photo cyclizations can be more selective than metal catalyzed electrophilic carbene cyclizations of the same analogs.


New Reactions and Methodology, Materials, Total Synthesis, Process R&D
8:00 PM-10:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- Hall A, Poster

8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005