Asymmetric synthesis of the interleukin-1b converting enzyme inhibitor (-)-EI-1941-2 using tandem oxaelectrocyclization/oxidation

ORGN 72

John A. Porco Jr., porco@bu.edu1, Andrew S. Kleinke, kleinke@bu.edu1, Chaomin Li, cl2350@columbia.edu1, and Nicolas Rabasso, nicorabasso@icmo.u-psud.fr2. (1) Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215, (2) Laboratoire des Carbocycles, Université Paris-Sud 11, Orsay, 91405, France
The total synthesis of the interleukin-1β converting enzyme inhibitor (-)-EI-1941-2 (1) will be described. This synthesis utilizes tartrate-mediated nucleophilic asymmetric epoxidation of a quinone monoketal for installation of the epoxide moiety. The key α-pyrone intermediate may be generated by a novel oxoammonium salt-mediated oxidation/oxaelectrocyclization/oxidation cascade. In this presentation, we will review the synthesis of (-)-EI-1941-2 as well as mechanistic studies related to the α-pyrone formation step.

 

Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- C302, Oral

Division of Organic Chemistry

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