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Mode of radicalcyclization (5-exovs. 6-endo) was investigated by using 6-(bromomethyl)dimethylsilyl derivatives of 1',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.

nucleic acids symposium series

Stereo- and regioselective radical cyclization of 6-(bromomethyl)dimethylsilyl-1',2'-unsaturated uracil nucleosides: Synthesis of 1'- -hydroxymethyl nucleosides