A concise synthesis of carolacton.
A synthesis of carolacton, a myxobacterial natural product that has profound effects on Streptococcus mutans biofilms, is reported. The synthesis proceeds via a longest linear sequence of 14 steps from an Evans β-ketoimide and enabled preliminary evaluations of the effects of late-stage intermediates on S. mutans biofilms. These studies suggest that further investigations into carolacton's structure-function relationships are warranted.
Department of Chemistry, Yale University , New Haven, Connecticut 06511, United States.
Michal S
MS
Hallside
Richard S
RS
Brzozowski
William M
WM
Wuest
Andrew J
AJ
Phillips
D018441:Biofilms / Q000187:drug effects; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry; D013295:Streptococcus mutans / Q000187:drug effects
D018942:Macrolides; C553423:carolacton