Metathesis and Heck strategies to bi- and tricyclic sultam libraries

ORGN 71

Dinesh K. Rayabarapu, drdinesh@ku.edu and Paul R. Hanson, phanson@ku.edu. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr, NIH Center of Excellence in Chemical Methodologies and Library Development (KU-CMLD), Lawrence, KS 66045-7582
The development of IMDA/metathesis strategies for the production of bi- and tricyclic sultams is reported. A tandem ring-opening/ring-closing/cross metathesis (ROM-RCM-CM) reaction has been accomplished affording tricyclic sultams. Utilization of ROM polymerization in a new atom-economical method employing reductive Heck on a bicyclic-norbornenyl sultam is also reported. This method allows for chromatography-free parallel processing of both reductive Heck product and excess sultam. In addition, intramolecular Heck, and lithiation pathways lead to versatile scaffolds, which undergo myriad transformations to afford highly functionalized sultams.

 

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