Total synthesis of the α-glucosidase inhibitors schulzeine B & C

ORGN 676

Duncan J. Wardrop, wardropd@uic.edu and Edward G. Bowen, wardropd@uic.edu. Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Room 4500, Chicago, IL 60607-7061
Since the discovery of nojirimycin, glycosidase inhibitors have become the subject of intense interest because of their profound effect on glycoprotein processing, oligosaccharide metabolism, and cell-cell and cell-virus recognition processes. The schulzeines, a novel class of tetrahydroisoquinoline alkaloids recently isolated by Fusetani and co-workers from the marine sponge Penares schulzei, display potent ?-glucosidase-inhibitory activity. Details of our enantioselective total synthesis of (-)-schulzeine B and (+)-schulzeine C will be presented. A key feature of this endeavor is the preparation of the benzo[a]quinolizidine “head” units through a diastereoselective Pictet-Spengler cyclocondensation. Total synthesis confirms that the structure of these unique marine natural products is, as previously proposed.

 

Asymmetric Reactions, Combinatorial Chemistry, Molecular Recognition and Self-Assembly, Proteins, Peptides, Amino Acids and Enzyme Inhibitors
8:00 PM-10:00 PM, Wednesday, March 28, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007