Concepedia

Synthesis and Antibacterial Properties of (−)-<i>nor</i>-Platencin

Olga V. Barykina, Kerri L. Rossi, Michael J. Rybak, Barry B. Snider

Organic Letters · 2009 · 39 citations · 38 references

Open access

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.

References

38

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Bioorganic Chemistry, Engineering, Antibiotic Adjuvant +20