A convergent synthetic approach to the nucleoside-type liposidomycin antibiotics.
[reaction: see text] A synthetic approach toward the liposidomycins, a family of complex nucleoside-type antibiotics, is reported based on the synthesis of epoxy-amides derived from the reaction of sulfur ylides with the uridyl aldehyde derivative 6. To this end, the epoxy-amide derivative of indoline 14 was stereoselectively prepared and, after treatment with DDQ, transformed into the corresponding N-indole epoxyamide 15. The indole 15 provides ready access to a variety of structures related to the diazepanone core present in the liposidomycins by reaction with a variety of amines.
Sarabia
Francisco
F
Departamento de Bioquímica, Biología Molecular y Química Orgánica, Facultad de Ciencias, Universidad de Málaga, 29071-Málaga, Spain. frsarabia@uma.es
Martín-Ortiz
Laura
L
López-Herrera
F Jorge
FJ
D000617:Aminoglycosides / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D008956:Models, Chemical; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D009705:Nucleosides; C047544:liposidomycins