Enantioselective synthesis of (+)-chamaecypanone C and analogs using a tandem retro-Diels-Alder/Diels-Alder cascade

ORGN 229

Suwei Dong, swdong@bu.edu1, Ernest Hamel2, John A. Beutler3, and John A. Porco Jr., porco@bu.edu1. (1) Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215, (2) Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick Cancer Research and Development Center, Frederick, MD 21702, (3) Molecular Targets Development Program, National Cancer Institute, Frederick Cancer Research and Development Center, Bldg.1052 Room 110, Frederick, MD 21702
The bicyclo[2.2.2]octenone-containing natural product chamaecypanone C ((+)-1) was isolated from the heartwood of Chamaecyparis obtusa var. formosana. Compound (+)-1 was shown to exhibit potent cytotoxicity against several human cancer cells including human oral epidermoid carcinoma (KB) (IC50 = 190 nM). In this presentation, we will describe our recent synthesis of (+)-1 and preparation of analogues employing a retro-DA/DA cascade as well as initial biological evaluation of the compounds.

 

Asymmetric Reactions and Syntheses
8:00 AM-11:40 AM, Monday, August 17, 2009 Walter E. Washington Convention Center -- 209A/B, Oral

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009