Toward a total synthesis of elenic acid: An inhibitor of topoisomerase II

ORGN 554

Kevin K. Tung, tung0018@umn.edu and Richard P. Hsung, hsung@chem.umn.edu. Department of Chemistry, University of Minnesota, Minneapolis, MN 55455
Elenic acid is an interesting synthetic compound because of the unusual structure among natural products and its proven potent biological activity. Elenic acid was isolated from the Indonesian sponge Plakinastrella sp. (0.012 wt%) and characterized by Scheuer and co-workers in 1995. Elenic acid has displayed cytotoxicity with IC50 of 5 µg/mL in P-388, A-549, and MEL-28 bioassays. It also inhibits topoiomerase II, which is an indicator enzyme in the treatment of lung cancer, at 0.1 µg/mL. Such activity compares favorably with clinical agents doxorubicin and etoposide. Finished reactions include mono-protection, functional group replacement, Wittig Olefination, deprotection, oxidation, hydrogenation, Grignard reaction. Several other transformations, such as Julia Olefination and Dess-Martin oxidation, are underway.

 

New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005