Rhodium-catalyzed allylic C-H activation and intramolecular hydroalkylation as a facile method of synthesis of pyrrolizidinone alkaloids

ORGN 570

Ashley S. Dumas, adumas@chm.uri.edu and Brenton DeBoef, bdeboef@chm.uri.edu. Department of Chemistry, University of Rhode Island, 51 Lower College Road, Pastore Laboratory, Kingston, RI 02881
The direct conversion of allylic C-H bonds to C-C bonds is a problem with few solutions. We are currently investigating possible solutions to this problem utilizing various rhodium catalysts to induce C-H activation and hydroalkylation of these allylic C-H bonds towards the synthesis of pyrrolizidinone alkaloids. Once optimal reaction conditions are established, these methods will be applied to the total synthesis of natural products, such as UCS1025A, a known telomerase inhibitor.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

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