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:: 10.1021/np2006555

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: Biomolecular Sciences Research Centre
Identification Number: 10.1021/np2006555
Depositing User: Marguerite Lyons
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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