Ring opening of 4',5'-epoxynucleosides: a novel stereoselective entry to 4'-C-branched nucleosides.

Org Lett

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

Published: May 2003

Stereoselective synthesis of 4'-alpha-carbon-substituted nucleosides has been accomplished through epoxidation of 4',5'-unsaturated nucleosides with dimethyldioxirane (DMDO) and successive SnCl(4)-promoted ring opening of the resulting 4',5'-epoxynucleosides with organosilicon reagents. [reaction: see text]

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http://dx.doi.org/10.1021/ol020259hDOI Listing

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