ROMP strategies in library development

ORGN 74

Toby R. Long, tbylong@ku.edu1, Dinesh K. Rayabarapu1, Maria Jimenez1, Josh Wewel2, Sarra Klimberg2, Paul R. Hanson, phanson@ku.edu1, and Daniel L. Flynn, dflynn@deciphera.com2. (1) 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, (2) Deciphera Pharmaceuticals LLC, 4950 Research Park Way, Lawrence, KS 66047
Methodologies incorporating ring-opening metathesis polymerization (ROMP) for use in library synthesis are reported. Utilization of a norbornenyl-tagged monochlorophosphate in capture-ROMP-cuprate-release protocols yields functionalized sultams and phosphonate scaffolds. Propargylated norbornenyl tags have also been developed for the incorporation of a Click-capture, diversify-release protocol to afford various triazoles. In addition, an atom-economical method has been developed whereby various reactions on an internally-armed bicyclic-norbornenyl sultam are coupled to ROM polymerization. This coupling allows for parallel processing of both sultam product as well as reclamation of excess sultam polymer which can be diversified and subjected to a vanishing support protocol.
 

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