Studies toward the asymmetric synthesis of the ambewelamides

ORGN 665

Andrew S. Kleinke, kleinke@bu.edu, Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Ave, Boston, MA 02215 and John A. Porco Jr., porco@bu.edu, Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215.
Studies toward the asymmetric syntheses of the epidithiodiketopiperazine-containing ambewelamides (scabrosin esters) will be described. Our synthesis utilizes chiral epoxyquinone monoketal building blocks generated from a tartrate-mediated nucleophilic asymmetric epoxidation. This presentation will review our efforts toward the development of novel methods for installation of the epidithiodiketopiperazine moiety as well as synthesis of advanced intermediates.

 

Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Wednesday, August 22, 2007 BCEC -- 258A, Oral

Division of Organic Chemistry

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