Synthesis of a new oxazolidinone antibacterial compound

ORGN 173

David Ebner, J. Thomas Ippoliti, and Jeff Cullhane. Department of Chemistry, University of St. Thomas, 2115 Summit Ave., OSS 402, St. Paul, MN 55105
The oxazolidinone class of antibiotics represents a promising advance in the fight against resistant Gram-positive bacterial infections. A novel oxazolidinone antibacterial compound containing a benzodioxin ring system has been prepared utilizing a seven-step synthesis. The synthesis begins with the construction of the benzodioxin ring system containing a nitro substituent that ultimately becomes the nitrogen of the oxazolidinone ring. The two oxygens of the benzodioxin ring system end up being ortho and para to the oxazolidinone ring nitrogen similar to the electron donating atoms of linezolid, the first oxazolidinone to be approved for use as an antibiotic.

 

Heterocycles and Aromatics
8:00 AM-12:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- 303D, Oral

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004