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A novel synthetic approach to(?)-Z-recifeiolide 6, a 12-membered-ring lactone which can be selectively isomerized into(E)-recifeiolide, a natural antibiotic product isolated from fungus(Cephalosporium recifei) is reported. The synthesis is accomplished in five steps starting from readily available cyclooctanone and acetaldehyde based on the Lewis acid-catalyzed TMS-directed oxy-2-oxonia-Cope rearrangement. The work represents a novel strategy to assemble related macrolides.
A novel synthetic approach to (?) - Z-recifeiolide 6, a 12-membered-ring lactone which can be selectively isomerized into (E) -recifeiolide, a natural antibiotic product isolated from fungus (Cephalosporium recifei) is reported. The synthesis is accomplished in five steps starting from both available cyclooctanone and acetaldehyde based on the Lewis acid-catalyzed TMS-directed oxy-2-oxonia-Cope rearrangement. The work represents a novel strategy to assemble related macrolides.