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Synthesis and antibacterial properties of (-)-nor-platencin.

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.

SUBMITTER: Barykina OV 

PROVIDER: S-EPMC2789445 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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Synthesis and antibacterial properties of (-)-nor-platencin.

Barykina Olga V OV   Rossi Kerri L KL   Rybak Michael J MJ   Snider Barry B BB  

Organic letters 20091101 22

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. ...[more]

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