Total synthesis of nucleoside antibiotics possessing novel N-glycoside structures

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Abstract

Construction of aryl and heteroaryl N-glycoside structures by way of the palladium-catalyzed Buchwald-Hartwig N-arylation of pyranosylamines with aryl and heteroaryl halide derivatives is described. This methodology was successfully applied to the total synthesis of nucleoside antibiotics, spicamycin and dapiramicin B, possessing novel heteroaryl N-glycosides. Kinetic and thermodynamic analyses of heteroaryl N-glycosides are also reported.

Original languageEnglish
Pages (from-to)1105-1115
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume66
Issue number11
Publication statusPublished - 2008 Nov

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Glycosides
Nucleosides
Anti-Bacterial Agents
Palladium
Thermodynamics
Derivatives
Kinetics

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "Construction of aryl and heteroaryl N-glycoside structures by way of the palladium-catalyzed Buchwald-Hartwig N-arylation of pyranosylamines with aryl and heteroaryl halide derivatives is described. This methodology was successfully applied to the total synthesis of nucleoside antibiotics, spicamycin and dapiramicin B, possessing novel heteroaryl N-glycosides. Kinetic and thermodynamic analyses of heteroaryl N-glycosides are also reported.",
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