Novel 9a,11-bridged azalides: One-pot synthesis of N'-substituted 2-imino-1,3-oxazolidines condensed to an azalide aglycone.
An efficient one-pot method for the synthesis of novel 9a,11-bridged 15-membered 9a-aza-9-deoxo-9a-homoerythromycin A and its 6-O-methyl analogue has been developed. The novel bicyclic azalide scaffold is characterized by an N'-substituted-2-imino-1,3-oxazolidine moiety bound to a macrolactone ring between positions 9a and 11. Removal of the cladinose sugar from the starting compounds allows easy preparation of a small series of such bicyclic 3-keto and 3,6-hemiketal azalide derivatives. A mechanism for the formation of N'-substituted-2-imino-1,3-oxazolidines is discussed. Antibacterial properties of the prepared compounds were evaluated.
GlaxoSmithKline Research Centre Zagreb, Prilaz B. Filipovića 29, Zagreb, Croatia.
Zorica Marušić
ZM
Ištuk
Ana
A
Cikoš
Dubravka
D
Gembarovski
Gorjana
G
Lazarevski
Ivica
I
Dilović
Dubravka
D
Matković-Čalogović
Goran
G
Kragol
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared
D001372:Aza Compounds; D010080:Oxazoles; C064210:oxazolidine