Synthesis of C3- epi -virenose and anomerically activated derivatives.

Autor: Röder L; Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria., Venegas ST; Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria., Wurst K; Department of General, Inorganic and Theoretical Chemistry, University of Innsbruck, 6020 Innsbruck, Austria., Magauer T; Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.
Jazyk: angličtina
Zdroj: Tetrahedron letters [Tetrahedron Lett] 2024 Apr; Vol. 140, pp. 155041.
DOI: 10.1016/j.tetlet.2024.155041
Abstrakt: A 9-step synthetic route to a protected form of the C3-epimer of virenose from D -fucose is described. C3- epi -virenose is the carbohydrate unit of the bioactive polyketide elsamicin B and part of the carbohydrate unit of elsamicin A. The developed route enabled preparation of anomerically activated forms of this unique C6-deoxy sugar, including derivatives with 1-acetyl, 1-acetylthio, 1-trichloroacetimidate, 1-bromo, and 1-fluoro substituents.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Databáze: MEDLINE
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