Synthesis and antibacterial properties of (-)-nor-platencin.
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.
Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Olga V
OV
Barykina
Kerri L
KL
Rossi
Michael J
MJ
Rybak
Barry B
BB
Snider
D000627:Aminophenols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013293:Enterococcus faecalis / Q000187:drug effects*; D016984:Enterococcus faecium / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects*; D013237:Stereoisomerism
D000627:Aminophenols; D000900:Anti-Bacterial Agents; D011083:Polycyclic Compounds; C520340:platencin