Issue 17, 2011
From the journal:

Organic & Biomolecular Chemistry

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

David Nečas,a   Denisa Hidasová,a   Michal Hocek*b  and  Martin Kotora*ab  

* Corresponding authors

a Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, Praha 2, Czech Republic
E-mail: kotora@natur.cuni.cz

b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, Praha 6, Czech Republic
E-mail: hocek@uochb.cas.cz

Abstract

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.

Graphical abstract: Modular synthesis of 1-α- and 1-β-(indol-2-yl)-2′-deoxyribose C-nucleosides

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Article information

DOI
https://doi.org/10.1039/C1OB05844D
Article type
Communication
Submitted
27 May 2011
Accepted
28 Jun 2011
First published
29 Jun 2011

Org. Biomol. Chem., 2011,9, 5934-5937

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

D. Nečas, D. Hidasová, M. Hocek and M. Kotora, Org. Biomol. Chem., 2011, 9, 5934 DOI: 10.1039/C1OB05844D

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