Compound libraries based on the Stemona alkaloid skeleton

ORGN 805

Kevin J Frankowski, vthokie@ku.edu, Chemical Methodology and Library Development Center of Excellence, University of Kansas, 1501 Wakarusa dr, Lawrence, KS 66049 and Jeffrey Aubé, jaube@ku.edu, Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Room 4070, Malott Hall, Lawrence, KS 66045-7582.
The reported antitussive activity of two Stemona alkaloids, neostenine and neotuberostemonine, inspired the synthesis of diversely-functionalized libraries based on the Stemona alkaloid core. Combining the Diels-Alder and azido Schmidt reactions provided access to the complex tricyclic skeleton of this class of alkaloids in an efficient and rapid manner. The tricyclic scaffolds were derivatized in parallel by either reductive amination or the Fischer indole synthesis. Screening these libraries will allow the exploration of the intricate relationship between molecular architecture and biological activity of this class of alkaloids.

 

Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007