First total synthesis of (±)-mitorubrinic acid

ORGN 895

Maurice A Marsini, mmarsini@chem.ucsb.edu and Thomas R. R. Pettus, pettus@chem.ucsb.edu. Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, CA 93106
The first total synthesis of (±)-mitorubrinic acid will be presented. The synthesis proceeds in 12 total steps and uses an oxidative dearomatization with ortho-iodoxybenzoic acid (IBX) to install the tertiary alcohol moiety of the azaphilone nucleus. While mitorubrinic acid itself does not display significant activity, its dimer, diazaphilonic acid, completely inhibits MTI (human leukemia telomerase) at an IC50 of 50 µM. Therefore, access to mitorubrnic acid is required for the synthesis of diazaphilonic acid, and work in this area will also be presented.
 

New Reactions and Methodology
8:00 AM-11:40 AM, Thursday, 14 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006