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Issue 8, 2014
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Synthesis of 4′-deoxy-4′-fluoro neamine and 4′-deoxy-4′-fluoro 4′-epi neamine

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Abstract

The syntheses of 4′-deoxy-4′-fluoro neamine and 4′-deoxy-4′-fluoro 4′-epi neamine from the readily available neamine and paromamine are described. Different approaches for the introduction of fluorine such as the use of DAST, sulfonic esters displacement, and epoxide ring opening by fluoride anion were studied. Examples of anchimeric assistance and ring contraction in the aminoglycoside series are highlighted.

Graphical abstract: Synthesis of 4′-deoxy-4′-fluoro neamine and 4′-deoxy-4′-fluoro 4′-epi neamine

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Supplementary files

Article information


Submitted
20 Feb 2014
Accepted
26 Mar 2014
First published
15 Apr 2014

Med. Chem. Commun., 2014,5, 1166-1171
Article type
Concise Article

Synthesis of 4′-deoxy-4′-fluoro neamine and 4′-deoxy-4′-fluoro 4′-epi neamine

S. Hanessian, O. M. Saavedra, M. A. Vilchis-Reyes and A. M. Llaguno-Rueda, Med. Chem. Commun., 2014, 5, 1166
DOI: 10.1039/C4MD00072B

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