Totalsynthese des Vancomycin- und des Eremomycin-Aglycons

Abstract

Die Kontrolle der Elemente planarer und axialer Chiralität ist die größte Herausforderung bei der Synthese des Aglycons von Vancomycin – Vancomycin ist der Prototyp einer Familie von Glycopeptid‐Antibiotika, die effektiv zur Behandlung von Infektionen durch das Methicillin‐resistente Bakterium Staphylococcus aureus eingesetzt werden. Die erste Totalsynthese des Vancomycin‐ und des Eremomycin‐Aglycons gibt Aufschluß über den Einfluß der Struktur auf die kinetische und thermodynamische Kontrolle der atropselektiven Makrocyclisierungen.

Mild Ullmann‐Type Biaryl Ether Formation Reaction by Combination of ortho‐Substituent and Ligand Effects

“…For elaboration of these synthetically challenging molecules, several elegant methods that feature biaryl ether formation have been developed. Examples include oxidative phenolic coupling,1c o ‐nitro‐1b, 2e, f, 7 or metal‐activated1c, 5a nucleophilic aromatic substitution, modified Ullmann‐type coupling reactions,1, 2a, 6 and boronic acid based biaryl ether synthesis 4. 8–10 However, more practical and flexible protocols are still required to improve the synthetic approaches to these biologically important cyclopeptides.…”

New Advances in the Biosynthesis of Glycopeptide Antibiotics of the Vancomycin Type fromAmycolatopsis mediterranei

“…[2] These assemblies often exhibit intense emissions, and the excited states are directly related to the Au´´´Au interaction. [5] The sparsity of homonuclear silver clusters may be attributed to the weaker metallophilic nature of silver compared to gold. [3] While the aurophilicity principle [4] has been used extensively to describe the strong, closed-shell metal ± metal interactions of gold clusters, surprisingly few examples of argentophilic behavior of closely related silver analogues have been reported.…”

Does CIP Nomenclature Adequately Handle Molecules with Multiple Stereoelements? A Case Study of Vancomycin and Cognates

“…In fact, the diaryl ether ring systems in all of the naturally occurring glycopeptide antibiotics possess the same configurations. Synthetic intermediates of vancomycin with either atropisomeric configuration have, however, been reported 7, 8, 22–25…”