Efforts toward the total synthesis of kendomycin

ORGN 406

Megan M Jacobson, mjacobson@wisc.edu, Department of Chemistry, University of Wisconsin - Madison, 1101 University Ave, Madison, WI 53706 and Steven D. Burke, burke@chem.wisc.edu, Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706.
Kendomycin is a natural product isolated from three different species of Strptomyces bacteria. It has significant activity as an antimicrobial agent against both Gram-positive and Gram-negative bacteria as well as antiosteoporotic and anticancer activity as an endothelin receptor antagonist. Efforts towards the total synthesis of Kendomycin will be discussed. The proposed synthetic route involves a longest linear sequence of 25 steps and features a spiroketalization/ring-closing methathesis sequence as a key step in the formation of the highly substituted tetrahydropyran ring.

 

New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007