Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations
Ryan J Beattie1, Thomas W Hornsby1, Gemma Craig1
1School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , UK . Email: m.c.galan@bristol.ac.uk ;
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.
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