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Synthesis and antibacterial properties of (-)-nor-platencin
Olga V Barykina1, Kerri L Rossi, Michael J Rybak
1Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Abstract:
An asymmetric Diels-Alder reaction between acrolein and 1-benzyloxymethyl-1,3-cyclohexadiene affords a bicyclic aldehyde that was elaborated in 11 steps to nor-platencin. nor-Platencin is 4-16 times less active than platencin against several resistant strains of Staphylococcus aureus, macrolide-resistant Enterococcus faecalis, and vancomycin-resistant Enterococcus faecium.
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