Modular synthesis of 1-α- and 1-β-(indol-2-yl)-2'-deoxyribose C-nucleosides.

David Nečas, Denisa Hidasová, Michal Hocek, Martin Kotora

Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43, Praha 2, Czech Republic.

Organic & biomolecular chemistry 2011 Sep 7

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A simple two-step method for the selective preparation of anomerically pure 1α- and 1β-(indol-2-yl)deoxyribose derivatives was developed. The synthesis was based on the Sonogashira reaction of 1α- and 1β-ethynyldeoxyribose and 2-haloanilines followed by a Pd-complex catalyzed cyclization to the corresponding indolyldeoxyribosides.

Citation

David Nečas, Denisa Hidasová, Michal Hocek, Martin Kotora. Modular synthesis of 1-α- and 1-β-(indol-2-yl)-2'-deoxyribose C-nucleosides. Organic & biomolecular chemistry. 2011 Sep 7;9(17):5934-7