Assembly of the Nosiheptide A-Ring: A Fruitful Lesson

Jin-Yong Lu; Matthias Riedrich; K. Philip Wojtas; Hans-Dieter Arndt

doi:10.1055/s-0032-1317810

Synthesis, Table of Contents

Synthesis 2013; 45(10): 1300-1311
DOI: 10.1055/s-0032-1317810

feature article

Assembly of the Nosiheptide A-Ring: A Fruitful Lesson

Jin-Yong Lu

^aTechnische Universität Dortmund, Fakultät Chemie, Otto-Hahn-Str. 6, 44221 Dortmund, Germany

^bMax-Planck-Institut für molekulare Physiologie, Otto-Hahn-Str. 11, 44227 Dortmund, Germany

,

Matthias Riedrich

^aTechnische Universität Dortmund, Fakultät Chemie, Otto-Hahn-Str. 6, 44221 Dortmund, Germany

^bMax-Planck-Institut für molekulare Physiologie, Otto-Hahn-Str. 11, 44227 Dortmund, Germany

,

K. Philip Wojtas

^cInstitut für Organische und Makromolekulare Chemie, Friedrich-Schiller-Universität, Humboldtstr. 10, 07743 Jena, Germany Fax: +49(3641)948212 Email: hd.arndt@uni-jena.de

,

Hans-Dieter Arndt*

^cInstitut für Organische und Makromolekulare Chemie, Friedrich-Schiller-Universität, Humboldtstr. 10, 07743 Jena, Germany Fax: +49(3641)948212 Email: hd.arndt@uni-jena.de

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Abstract

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Abstract

The synthesis of a 28-membered thiopeptide macrocycle is described. Key steps are mild aza-Wittig thiazole ring closures, a scandium(III)-mediated regioselective ester hydrolysis, and a highly efficient macrolactam formation with its 3-hydroxypyridine nucleus orthogonally protected.

Key words

antibiotics - aza-Wittig reaction - heterocycles - natural products - macrocyclization - thiopeptides.

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References

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Supplementary Material

Supporting Information