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Issue 4, 2016
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Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations

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Abstract

A de novo approach for the rapid construction of orthogonally protected L- and D-deoxysugars and analogues is described. A novel and robust silicon-acetal undergoes Prins cyclisations with a series of homoallylic alcohols in high yield and excellent stereocontrol. Modified Tamao–Fleming oxidation of the resulting silyltetrahydropyrans gives direct access to deoxyglycoside analogues and the approach was showcased in the synthesis of protected L-oliose, a component of the anticancer agent aclacinomycin A.

Graphical abstract: Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations

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Supplementary files

Article information


Submitted
01 Nov 2015
Accepted
08 Jan 2016
First published
11 Jan 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 2743-2747
Article type
Edge Article
Author version available

Stereoselective synthesis of protected L- and D-dideoxysugars and analogues via Prins cyclisations

R. J. Beattie, T. W. Hornsby, G. Craig, M. C. Galan and C. L. Willis, Chem. Sci., 2016, 7, 2743
DOI: 10.1039/C5SC04144A

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