Issue 22, 2010
From the journal:

Organic & Biomolecular Chemistry

Synthesis of C-6-substituted uridine phosphonates through aerobic ligand-free Suzuki–Miyaura cross-coupling†‡

Radim Nencka,ab   Davy Sinnaeve,c   Izet Karalic,a   José C. Martinsc  and  Serge Van Calenbergh*a  

* Corresponding authors

a Laboratory for Medicinal Chemistry, Faculty of Pharmaceutical Sciences (FFW), Ghent University, Harelbekestraat 72, Ghent, Belgium
E-mail: serge.vancalenbergh@ugent.be
Fax: +32 9 2648146
Tel: +32 9 2648124

b Centre for New Antivirals and Antineoplastics, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic, v.v.i.(IOCB), Gilead & IOCB Research Center, Prague 6, Czech Republic
E-mail: nencka@uochb.cas.cz
Fax: +420 220183560
Tel: +420 220183323

c NMR and Structure Analysis Unit, Department of Organic Chemistry, Ghent University, Krijgslaan 281 S4, Ghent, Belgium
E-mail: jose.martins@ugent.be
Fax: +32 9 2644972

Abstract

An efficient protocol for the construction of C-6-(hetero)aryl-substituted uridine phosphonate analogues utilizing an aerobic, ligand-free Suzuki–Miyaura cross-coupling reaction of a 6-iodo-precursor in aqueous media has been established. The method presents a modular approach toward the target compounds as demonstrated by the synthesis of a small library comprising 14 novel nucleoside phosphonates.

Graphical abstract: Synthesis of C-6-substituted uridine phosphonates through aerobic ligand-free Suzuki–Miyaura cross-coupling

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Article information

DOI
https://doi.org/10.1039/C0OB00061B
Article type
Paper
Submitted
29 Apr 2010
Accepted
17 Aug 2010
First published
21 Sep 2010

Org. Biomol. Chem., 2010,8, 5234-5246

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Synthesis of C-6-substituted uridine phosphonates through aerobic ligand-free Suzuki–Miyaura cross-coupling

R. Nencka, D. Sinnaeve, I. Karalic, J. C. Martins and S. Van Calenbergh, Org. Biomol. Chem., 2010, 8, 5234 DOI: 10.1039/C0OB00061B

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