Expeditious Synthesis of Ieodoglucomides A and B from the Marine‐Derived Bacterium Bacillus licheniformis

We report the total synthesis of ieodoglucomides A and B. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The short and efficient synthesis invo...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:European journal of organic chemistry 2018-06, Vol.2018 (24), p.3230-3235
Hauptverfasser: Podilapu, Ananda Rao, Emmadi, Madhu, Kulkarni, Suvarn S.
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:We report the total synthesis of ieodoglucomides A and B. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The short and efficient synthesis involves 11 steps, with 38–40 % overall yield. The total synthesis of the marine‐derived bacterial glycopeptides ieodoglucomides A and B is reported. The key steps of the synthesis are a glycosyl‐iodide‐mediated β‐stereoselective glycosylation without neighbouring‐group participation, a regioselective acylation, and a Grubbs cross‐metathesis reaction. The synthesis involves 11 steps, with 38–40 % overall yield.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800209