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

Org Lett

Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.

Published: November 2009

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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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2789445PMC
http://dx.doi.org/10.1021/ol902194qDOI Listing

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