Synlett 2018; 29(04): 440-446
DOI: 10.1055/s-0036-1591517
letter
© Georg Thieme Verlag Stuttgart · New York

Thieme Chemistry Journals Awardees – Where Are They Now? ­Ribosylation of an Acid-Labile Glycosyl Acceptor as a Potential Key Step for the Synthesis of Nucleoside Antibiotics

Daniel Wiegmann
a  Saarland University, Department of Pharmacy, Pharmaceutical and Medicinal Chemistry, Campus C2 3, 66123 Saarbrücken, Germany   eMail: [email protected]
,
Anatol P. Spork
b  Georg-August-University Göttingen, Department of Chemistry, Institute of Organic and Biomolecular Chemistry, Tammannstr. 2, 37077 Göttingen, Germany
,
a  Saarland University, Department of Pharmacy, Pharmaceutical and Medicinal Chemistry, Campus C2 3, 66123 Saarbrücken, Germany   eMail: [email protected]
,
a  Saarland University, Department of Pharmacy, Pharmaceutical and Medicinal Chemistry, Campus C2 3, 66123 Saarbrücken, Germany   eMail: [email protected]
b  Georg-August-University Göttingen, Department of Chemistry, Institute of Organic and Biomolecular Chemistry, Tammannstr. 2, 37077 Göttingen, Germany
› Institutsangaben
We thank the Deutsche Forschungsgemeinschaft (DFG, SFB 803 ‘Functionality controlled by organization in and between membranes’ and grant DU 1095/5-1) and the Fonds der Chemischen Industrie (FCI, Sachkostenzuschuss) for financial support. D. W. is grateful for a doctoral fellowship of the Konrad-Adenauer-Stiftung. G. N. is grateful for a doctoral fellowship of the FCI.
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Publikationsverlauf

Received: 05. Oktober 2017

Accepted after revision: 06. Oktober 2017

Publikationsdatum:
12. Dezember 2017 (online)


Dedicated to Professor Joachim Thiem on the occasion of his birthday.

Abstract

Naturally occurring nucleoside antibiotics (e.g., muraymycins and caprazamycins) represent attractive lead structures for the development of urgently needed novel antibacterial agents. One major challenge in the total synthesis of muraymycins, caprazamycins, and their analogues is the efficient construction of the densely functionalized aminoribosylated uridine-derived core unit. In order to avoid tedious protecting-group manipulations, we have aimed to conduct the aminoribosylation step with an acid-labile glycosyl acceptor. Therefore, different glycosylation approaches have been studied, with pentenyl glycosides giving the best results.

Supporting Information

 
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