Stereocontrolled Synthesis of 5′- and 6′-Epimeric Analogues of Muraymycin Nucleoside Antibiotics

Anatol P. Spork; Christian Ducho

doi:10.1055/s-0032-1318117

Synlett, Table of Contents

Synlett 2013; 24(3): 343-346
DOI: 10.1055/s-0032-1318117

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Stereocontrolled Synthesis of 5′- and 6′-Epimeric Analogues of Muraymycin Nucleoside Antibiotics

Anatol P. Spork

University of Paderborn, Department of Chemistry, Warburger Str. 100, 33 098 Paderborn, Germany Fax: +49(5251)603245 Email: christian.ducho@uni-paderborn.de

,

Christian Ducho*

University of Paderborn, Department of Chemistry, Warburger Str. 100, 33 098 Paderborn, Germany Fax: +49(5251)603245 Email: christian.ducho@uni-paderborn.de

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Abstract

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Abstract

Naturally occurring nucleoside antibiotics, for example, Streptomyces-produced muraymycins, represent a promising class of potential lead structures for the development of novel antimicrobial agents. The efficient preparation of muraymycin analogues is an essential prerequisite for detailed structure–activity relationship (SAR) studies, particularly with respect to the variation of the stereochemistry in a controlled manner. In this work, stereoselective syntheses of 5′- as well as 6′-epimers of muraymycins are reported. The obtained target structures also represent useful probes for the elucidation of the biosynthesis of muraymycins and related nucleoside antibiotics.

Key words

antibiotics - medicinal chemistry - natural products - nucleosides - biosynthesis

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References

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