Synthesis of C3--virenose and anomerically activated derivatives.

Tetrahedron Lett

Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.

Published: April 2024

A 9-step synthetic route to a protected form of the C3-epimer of virenose from -fucose is described. C3--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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7615872PMC
http://dx.doi.org/10.1016/j.tetlet.2024.155041DOI Listing

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