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.
PROVIDER: S-EPMC5477037 | BioStudies |
REPOSITORIES: biostudies
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