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The Cohalogenation of 1-N-Vinylpyrimidinediones: A New Approach to Nucleoside Analogs

✍ Scribed by Nathalie Baret; Jean-Pierre Dulcere; Jean Rodriguez; Jean-Marc Pons; Robert Faure

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
449 KB
Volume
2000
Category
Article
ISSN
1434-193X

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✦ Synopsis

A new approach to the synthesis of nucleoside analogs has been developed, which involves initial chemo-and regioselective cohalogenation of 1-N-vinylpyrimidinediones 10a,b using N-bromosuccinimide in the presence of variously substituted propargylic alcohols. Radical carbocyclization of the resulting Ξ²-bromo propargylic ethers 17-22 then leads to 3methylenetetrahydrofurans 23-26. In such cyclizations, different reactivities have been observed for diastereomers [a]

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