One-pot syntheses of pseudopteroxazoles from pseudopterosins : a rapid route to non-natural congeners with improved antimicrobial activity

MCCULLOCH, Malcolm W. B., BERRUE, Fabrice, HALTLI, Brad and KERR, Russell G. (2011). One-pot syntheses of pseudopteroxazoles from pseudopterosins : a rapid route to non-natural congeners with improved antimicrobial activity. Journal of Natural Products, 74 (10), 2250-2256.

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Official URL: http://dx.doi.org/10.1021/np2006555
Link to published version:: https://doi.org/10.1021/np2006555
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    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.

    Item Type: Article
    Research Institute, Centre or Group - Does NOT include content added after October 2018: Biomolecular Sciences Research Centre
    Identification Number: https://doi.org/10.1021/np2006555
    Page Range: 2250-2256
    Depositing User: Users 3084 not found.
    Date Deposited: 10 May 2013 08:50
    Last Modified: 10 May 2013 08:50
    URI: http://shura.shu.ac.uk/id/eprint/7006

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