Journal
JOURNAL OF NATURAL PRODUCTS
Volume 74, Issue 10, Pages 2250-2256Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np2006555
Keywords
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Funding
- Natural Sciences and Engineering Council of Canada (NSERC)
- Canada Research Chair Program
- Atlantic Innovation Fund
- Jeanne and Jean-Louis Levesque Foundation
- National Research Council
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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.
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