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Nucleic Acids Symposium Series 2001 1(1):3-4; doi:10.1093/nass/1.1.3
© 2001 by Oxford University Press
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Stereo- and regioselective radical cyclization of 6-(bromomethyl)dimethylsilyl-1',2'-unsaturated uracil nucleosides: Synthesis of 1'-{alpha}-hydroxymethyl nucleosides

Junko Ogamino, Hiroki Kumamoto, Hidenori Mizunuma, Shingo Takeda and Hiromichi Tanaka

School of Pharmaceutical Sciences, Showa University, 1-5-8 Shinagawa-ku, Tokyo 142-8555, Japan

Mode of radicalcyclization (5-exovs. 6-endo) was investigated by using 6-(bromomethyl)dimethylsilyl derivatives of l',2'-unsaturated uridine with an aim to develop a new stereoselective method for the introduction of an {alpha}-hydroxymethyl group at the anomeric position. Although the 2'-unsubstituted derivative underwent only 6-endo-cyclization, substrates bearing 2'-CO2Me or 2'-OBz group gave exclusively 5-exo-cyclized products with a high stereoselectivity.


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