Synthetic strategy for polyhydroxylated indolizidine iminosugar from sugar-derived HWE precursor

The diversity of polyhydroxylated indolizidine (PI) iminosugars is ever-expanding due to the wide range of methods developed and substrate choice during synthesis. This study used an HWE precursor derived from d-glucose to extend the chain length at the C1 position. A double reductive amination and...

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Bibliographic Details
Published inCarbohydrate research Vol. 545; p. 109302
Main Authors Ingaladal, Nagaraja, Lankalapalli, Ravi S.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.11.2024
Subjects
Bicyclic iminosugar
C-glycoside
Double reductive amination
HWE reaction
Mitsunobu reaction
Polyhydroxylated indolizidine
HWE reaction
Bicyclic iminosugar
Double reductive amination
C-glycoside
Polyhydroxylated indolizidine
Mitsunobu reaction
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Summary:The diversity of polyhydroxylated indolizidine (PI) iminosugars is ever-expanding due to the wide range of methods developed and substrate choice during synthesis. This study used an HWE precursor derived from d-glucose to extend the chain length at the C1 position. A double reductive amination and dihydroxylation of the resulting olefin, followed by intramolecular cyclization, enabled the successful synthesis of a new PI. In addition, the precursor intermediate for Mitsunobu reaction was utilized in synthesis of a new iminononulol. [Display omitted] •This study describes a methodology for synthesizing a new polyhydroxylated indolizidine iminosugar from an HWE precursor.•The methodology also enabled the synthesis of a new iminononulol.•The enone generated from the HWE reaction can be used in 1,4-Michael addition reactions to increase the diversity of polyhydroxylated indolizidines.
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ISSN:0008-6215
1873-426X
1873-426X
DOI:10.1016/j.carres.2024.109302