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

Ryan J. Beattie, Tom Hornsby, Gemma Craig, M. Carmen Galan*, Christine L. Willis

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

13 Citations (Scopus)
246 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)2743-2747
Number of pages5
JournalChemical Science
Volume7
Issue number4
Early online date11 Jan 2016
DOIs
Publication statusPublished - 1 Apr 2016

Structured keywords

  • BCS and TECS CDTs

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