Two convergent approaches toward novel carbocyclic C-nucleosides

0351443 - ÚOCHB 2011 RIV DE eng J - Journal Article
Nencka, Radim - Šála, Michal - Dejmek, Milan - Dračínský, Martin - Holý, Antonín - Hřebabecký, Hubert
Two convergent approaches toward novel carbocyclic C-nucleosides.
Synthesis. -, č. 23 (2010), s. 4119-4130. ISSN 0039-7881. E-ISSN 1437-210X
R&D Projects: GA MŠMT 1M0508
Institutional research plan: CEZ:AV0Z40550506
Keywords : carbocyclic C-nucleosides * convergent approach * uracil * pyrimidines
Subject RIV: CC - Organic Chemistry
Impact factor: 2.260, year: 2010

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.
Permanent Link: http://hdl.handle.net/11104/0191197