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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.

SUBMITTER: Beattie RJ

PROVIDER: S-EPMC5477037 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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Stereoselective synthesis of protected l- and d-dideoxysugars and analogues <i>via</i> Prins cyclisations.

Beattie Ryan J RJ Hornsby Thomas W TW Craig Gemma G Galan M Carmen MC Willis Christine L CL

Chemical science 20160111 4

A <i>de novo</i> 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 a ...[more]

PMID: 28660050

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