Issue 25, 2010
From the journal:

Chemical Communications

A stereocontrolled method for the synthesis of d- and l-2-deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction†

Rebecca R. Midtkandal,a   Simon J. F. Macdonaldb  and  Marie E. Migaud*a  

* Corresponding authors

a Queen's University Belfast, School of Chemistry and Chemical Engineering, Belfast, UK
E-mail: m.migaud@qub.ac.uk

b GlaxoSmithKline, Stevenage Pharmaceuticals R&D facility, Gunnels Wood Road, Stevenage, Herts, UK

Abstract

A novel synthetic procedure has been developed that provides access to D/L-2-deoxy-C-nucleosides from 3,4-epoxytetrahydrofuran in seven steps and in moderate to good yields. The key chemical transformation was the Lewis acid catalysed intramolecular cyclisation reaction of an acetal for which the stereochemical outcome was dependent of the reagents' ratio.

Graphical abstract: A stereocontrolled method for the synthesis of d- and l-2-deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction

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Article information

DOI
https://doi.org/10.1039/C0CC00467G
Article type
Communication
Submitted
18 Mar 2010
Accepted
26 Apr 2010
First published
20 May 2010

Chem. Commun., 2010,46, 4538-4540

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A stereocontrolled method for the synthesis of D- and L-2-deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction

R. R. Midtkandal, S. J. F. Macdonald and M. E. Migaud, Chem. Commun., 2010, 46, 4538 DOI: 10.1039/C0CC00467G

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