Asymmetric synthesis of substituted tropinones using the intramolecular Mannich cyclization reaction and acyclic N-sulfinyl -amino ketone ketals

ORGN 665

Franklin A. Davis,, Naresh Theddu,, and Paul M. Gaspari, Department of Chemistry, Temple University, 13th and Norris street, Philadelphia, PA 19122
The tropane alkaloids contain a common structural unit, the 8-azabicyclo[3.2.1]octane ring system. Because of their biological importance these alkaloids have generated much interest in new methods for their asymmetric synthesis. Described here is a general approach for the asymmetric synthesis of ring-substituted tropinones. Hydrolysis of enantiopure acyclic N-sulfinyl -amino ketone ketals affords dehydropyrrolidines. On treatment with p-NO2-Bz-Cl or (Boc)2O/cat.-DMAP these dehydropyrrolidines undergo an intramolecular Mannich cyclization to give the tropinones in good yield and high selectivity. These and other results will be presented.


Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

8:00 PM-10:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009