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Synthesis and Antibacterial Properties of (−)-nor-Platencin

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journal contribution
posted on 2009-11-19, 00:00 authored by Olga V. Barykina, Kerri L. Rossi, Michael J. Rybak, Barry B. Snider
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.