Synthetic approaches to Artemisinin-related natural products, Dihydroartemisinic Acid and Arteannuin M

ORGN 477

Douglas A. Engel, Engel22GL@aol.com, Hubert T. C. Lam, hlam@chem.fsu.edu, Jeananne Singletary, Kevin W. C. Poon, poon@chem.fsu.edu, and Gregory B. Dudley, gdudley@chem.fsu.edu. Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306
Artemisinin is a key compound for the treatment of malaria and an experimental cancer drug, but natural supplies are inadequate to meet the global demand. We are investigating synthetic approaches to dihydroartemisinic acid (a known precursor to artemisinin) and arteannuin M that are intended to provide a better source of these compounds and, by extension, to artemisinin. A key step in our approach is a two-step olefination of a hindered ketone that makes use of the Meyer-Schuster rearrangement, which prompts a methodological investigation of this underdeveloped reaction. Synthetic progress will be reported.

 

Total Synthesis of Complex Molecules
1:00 PM-5:20 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- C301, Oral

Division of Organic Chemistry

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