Progress toward a convergent synthesis of ustiloxin D

ORGN 796

Pixu Li, lipixu@sas.upenn.edu, Cory D. Evans, cyevans@sas.upenn.edu, and Madeleine M. Joulli, mjoullie@sas.upenn.edu. Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, PA 19104
The ustiloxins are a family of heterodetic cyclopeptides that have been isolated from the water extracts of false smut balls on the panicles of rice plants caused by a fungus Ustilaginoidea virens. Biological evaluation showed that ustiloxins are potent tubulin inhibitors. The ustiloxins contain a common 13-membered peptide macrocycle with a chiral tertiary alkyl-aryl ether linkage. Two total syntheses of ustiloxin D have been reported to date. Development of a new method for the construction of chiral tertiary alkyl-aryl ethers, as well as a convergent approach to ustiloxin D based on the method, will be described.
 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

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