Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers

The proposed diastereoisomers (1 a–d) together with their C8′‐epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to b...

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Bibliographic Details
Published in:Angewandte Chemie 2018-03, Vol.130 (11), p.2934-2938
Main Authors: Wang, Shengyang, Sun, Jiansong, Zhang, Qingju, Cao, Xin, Zhao, Yachen, Tang, Gongli, Yu, Biao
Format: Article
Language:English
Subjects:
Aldehydes
Amino acids
Aminosäuren
Antibiotics
Antibiotika
Chemistry
Configurations
Diastereoisomers
Fungicides
Glycosylation
Glykosylierungen
Gold
Naturstoffe
NMR
Nuclear magnetic resonance
Nucleosides
Sugar
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Summary:The proposed diastereoisomers (1 a–d) together with their C8′‐epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio‐ and stereocontrolled gold(I)‐catalyzed N‐glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be of opposite configuration. Umkonfiguriert: Die vorgeschlagenen Diastereomere und die entsprechenden C8′‐Epimere des Peptidylnukleosid‐Antibiotikums Amipurimycin wurden synthetisiert. Eine Analyse der NMR‐Daten deutet darauf hin, dass das tertiäre C3′ in Amipurimycin die entgegengesetzte Konfiguration haben sollte als früher postuliert.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201800169