Synthesis of 4′-deoxy-4′-fluoro neamine and 4′-deoxy-4′-fluoro 4′-epi neamine†,10.1039/C4MD00072B

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

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

Stephen Hanessian,Oscar M. Saavedra,Miguel A. Vilchis-Reyes,Ana M. Llaguno-Rueda

MedChemComm Pub Date : 04/15/2014 00:00:00 , DOI:10.1039/C4MD00072B

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.