Asymmetric synthesis of pseudodistomin E from N-sulfinyl d-amino b-ketoester enaminones

ORGN 125

Alexander Augustine, alexaug@temple.edu, Franklin A. Davis, fdavis@temple.edu, and Junyi Zhang. Department of Chemistry, Temple University, Philadelphia, PA 19122
N-Sulfinyl d-amino b-ketoester enaminones 1, undergo an intramolecular Michael addition followed by a retro-Michael type elimination upon one pot hydrolysis, to give enantiopure 2,4,5-trisubstituted-2,3-dihydropyridones. These dihydropyridones can be transformed into the corresponding all cis-2,4,5-trisubstituted piperidines by hydrogenation and controlled borohydride reduction. Utilization of this methodology led to the first asymmetric syntheses of the marine alkaloid pseudodistomin E, a potential anti-tumor agent.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006