General strategies for the enantioslective construction of pyrrolidine-based alkaloids: Total synthesis of (+)-cis-pyrrolidine 225H

ORGN 123

April Noble, arnoble@uno.edu and Mark L. Trudell, mtrudell@uno.edu. Department of Chemistry, University of New Orleans, 2000 Lakeshore Drive, New Orleans, LA 70148
Amphibian alkaloids are attractive targets for the development of therapeutic agents due to their structural diversity and unique pharmacological profiles. An important class of amphibian alkaloids is the 2,5-disubstituted pyrrolidine-based compounds. There are many synthetic approaches for the preparation of the trans-2,5-disubstituted pyrrolidines, but methods for the construction of the cis-2,5-disubstituted pyrrolidine ring system are limited. To this end, an enantioselective approach for the preparation of cis-2,5-disubsituted pyrrolidine has been developed from Cocaine. To demonstrate the scope and utility of cocaine derived building blocks for synthesis, the enantioselective total synthesis of cis-2,5-pyrrolidine alkaloid 22H has been completed in 10 steps and 29% overall yield.

 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008