New derivatives of tylosin: chemical and electrochemical oxidation products of desmycosin.
Chemical and electrochemical oxidation of dienonic moiety of desmycosin were carried out. Successive chemical oxidation of desmycosin with m-chloroperbenzoic acid afforded a family of 12,13-dihydro-12,13-dihydroxy derivatives. Indirect electrochemical oxidation via hypobromite as an intermediate gave rise to the new bicyclo derivative of desmycosin, 13-hydroxy-3-dehydroxy-3,12-oxa-desmycosin.
Mandić
Z
Z
PLIVA Research Division, Pharm. Ind. Inc., Prilaz b. Filipovića 25, HR-I0000 Zagreb, Croatia. Zoran.Mandic@pliva.hr
Naranda
A
A
Novak
P
P
Brajsa
K
K
Derek
M
M
Iveković
D
D
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D001419:Bacteria / Q000187:drug effects; D004563:Electrochemistry; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010084:Oxidation-Reduction; D015645:Tylosin / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology
C469533:13-hydroxy-3-dehydroxy-3,12-oxa-desmycosin; D000900:Anti-Bacterial Agents; C052318:tylosin B; D015645:Tylosin