Pd-catalyzed C-C bond forming reactions of a thymidine arylsulfonate

ORGN 553

Soon Bang Kang, u04183@sci.ccny.cuny.edu, Life Sciences Research Division, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul, 136-791, South Korea, Erik De Clercq, Rega Institute for Medical Research, Minderbroedersstraat 10, B-3000, Leuven, Belgium, and Mahesh K. Lakshman, lakshman@sci.ccny.cuny.edu, Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, NY 10031-9198.
The Suzuki-Miyaura reactions of halo nucleoside derivatives with arylboronic acids provide facile access to aryl-linked nucleoside analogues. Use of arylsulfonate derivatives for these reactions has begun to receive attention due to the ease of their synthesis. Presented herein are our results on the Pd-catalyzed Suzuki-Miyaura cross coupling of an O4-arylsulfonate derivative of thymidine with arylboronic acids under mild conditions. Results show that there is interplay between several parameters for successful reaction. The effect of various reaction parameters on the C-C bond-forming reactions of the thymidine O4-arylsulfonate with arylboronic acids and the anti-viral screening results of the corresponding C-4 aryl pyrimidinone nucleoside analogues will be presented.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007