Issue 4, 2016

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2016,7, 2743-2747

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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