Metathesis strategies in synthesis: Phosphorus heterocycles and functional oligomers

ORGN 45

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
Utilization of ring-closing metathesis (RCM) to construct novel phosphorus-containing heterocycles (P-heterocycles) for use in natural product synthesis, and use of ring-opening metathesis polymerization (ROMP) for the production of high-load oligomeric reagents will be discussed. Combination of RCM and various P-tethers allows for the facile construction of unique P-heterocycles. Overall, the method demonstrates a fundamentally new role of phosphates in synthesis and provides differentiated polyol building blocks for use in natural product synthesis.

In addition, the development of several high-load oligomeric reagents via ROM polymerization of norbornenyl–tagged monomers will be reported. These oligomers are stable, free flowing powders that display a wide solubility profile. Moreover, they have been exploited in facilitated synthetic protocols whereby simple precipitation/filtration of the reaction byproducts is the sole purification protocol. Efforts at developing polymer-on-polymer (PoP) protocols will also be discussed.

 

Recent Developments in Metathesis-Related Processes
1:00 PM-5:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- C303/304/305, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006