Aqueous Wittig reactions and the application toward the synthesis of streptogramin type A antibiotics

ORGN 476

Robert J. Anness, propaganda99@cox.net, Wen Zhao, wenzhao@ucsd.edu, Amer El-Batta, amerhajjawi@yahoo.com, Changchun Jiang, chjiang99@yahoo.com, and Mikael Bergdahl, bergdahl@sciences.sdsu.edu. Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Dr, San Diego, CA 92182
Wittig reactions have been conducted in water and several examples are presented. The modified Wittig conditions have been used to prepare a key fragment of Virginimycin M1. Water is as an excellent medium for the Wittig reactions employing stabilized ylides and aldehydes. The reactions presented are also compared to those conducted in conventional organic solvents. Excellent yields as well as E/Z-ratios of the desired products are presented.
 

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

Division of Organic Chemistry

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