title: One-pot syntheses of pseudopteroxazoles from pseudopterosins: a rapid route to non-natural congeners with improved antimicrobial activity.
abstract: Rapid one-pot methodologies to prepare pseudopteroxazole (1) and novel congeners from abundant natural pseudopterosins have been devised. This is highlighted here with the first synthesis of the marine natural product homopseudopteroxazole (2) utilizing a novel, silver(I)-mediated catechol to benzoxazole transformation. Pseudopteroxazoles and isopseudopteroxazoles exhibit potent activity against a range of important Gram-positive pathogens including Mycobacterium spp. and vancomycin-resistant Enterococcus faecium. Several non-natural pseudopteroxazoles exhibited strong activity against methicillin-resistant Staphylococcus aureus, thereby displaying a broader spectrum of antibiotic activity compared to pseudopteroxazole.
authors: Department of Chemistry, Atlantic Veterinary College, University of Prince Edward Island, Charlottetown, PEI C1A 4P3, Canada.
authors: Malcolm W B
authors: MW
authors: McCulloch
authors: Fabrice
authors: F
authors: Berrue
authors: Brad
authors: B
authors: Haltli
authors: Russell G
authors: RG
authors: Kerr
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D016984:Enterococcus faecium / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry*; D016106:Methicillin Resistance / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D014640:Vancomycin / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D004224:Diterpenes; D006027:Glycosides; D010080:Oxazoles; C049922:pseudopterosins; C433836:pseudopteroxazole; D014640:Vancomycin