Synthesis of C3- epi-virenose and anomerically activated derivatives

  • Tetrahedron Lett. 2024 Apr:140:155041. doi: 10.1016/j.tetlet.2024.155041.
Liesa Röder  #  1 ,  Sofia Torres Venegas  #  1 ,  Klaus Wurst  2 ,  Thomas Magauer  1
Affiliations
  • 1. Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.
  • 2. Department of General, Inorganic and Theoretical Chemistry, University of Innsbruck, 6020 Innsbruck, Austria.
  • # Contributed equally.
PMID: 38665383 DOI: 10.1016/j.tetlet.2024.155041
Abstract

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.

Keywords
Anomeric activation; Bioactive natural products; C3-epi-virenose; Carbohydrate synthesis.
Products