A convergent ring-closing metathesis approach to carbohydrate-based macrolides with potential antibiotic activity.
[reaction: see text] An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against gram-positive and gram-negative bacteria, including resistant strains, yeasts, and molds.
Blom
Petra
P
Laboratory for Organic and Bioorganic Synthesis, Department of Organic Chemistry, Ghent University, Krijgslaan 281 (S.4), B-9000 Gent, Belgium.
Ruttens
Bart
B
Van Hoof
Steven
S
Hubrecht
Idzi
I
Van der Eycken
Johan
J
Sas
Benedikt
B
Van hemel
Johan
J
Vandenkerckhove
Jan
J
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002241:Carbohydrates / Q000737:chemistry*; D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D002241:Carbohydrates; D018942:Macrolides