Synthetic studies of erythromycin derivatives. Synthesis and antimicrobial activities of 3''-EPI-erythromycin A and (9S)-11-dehydroxy-9-deoxo-9-hydroxy-11- oxoerythromycin A.
Two new derivatives, 3''-epi-erythromycin A (2) and (9S)-11-dehydroxy-9-deoxo-9-hydroxy-11-oxoerythromycin A (3), have been synthesized by using glycosylation with glycal (Ferrier rearrangement), bromomethoxylation and bis(tributyltin) oxide-bromine oxidation as the key steps. Their antimicrobial activities were compared with those of erythromycin A (1).
Nakata
M
M
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
Tamai
T
T
Miura
Y
Y
Kinoshita
M
M
Tatsuta
K
K
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests
D000900:Anti-Bacterial Agents; C081742:11-dehydroxy-9-deoxo-9-hydroxy-11-oxoerythromycin A; D004917:Erythromycin