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DOI: 10.1055/s-0030-1258271
Two Convergent Approaches toward Novel Carbocyclic C-Nucleosides
Publication History
Received
3 August 2010
Publication Date:
28 September 2010 (online)


Abstract
Two convergent methodologies for construction of novel carbocyclic C-nucleosides allowing the syntheses of derivatives with uracil heterobase substituted at the position C-5 as well as C-6 were developed. The crucial step of the first methodology was the reaction of (6-chloro-2,4-dimethoxypyrimidin-5-yl)lithium, the nucleobase precursor, with suitable ketones, the carbocyclic pseudosugar precursors. The second approach was based on the copper-catalyzed cross-coupling between magnesiated pyrimidine and appropriate allyl chlorides. These methodologies were applied for the synthesis of novel carbocyclic C-nucleosides bearing cyclohexene or cyclohexane as a pseudosugar.
Key words
carbocyclic C-nucleosides - convergent approach - uracil - pyrimidines - cross-coupling reaction
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