New dihydro and tetrahydro derivatives of desmycosin. III. The opening of oxirane ring of 12,13-epoxydesmycosin.
Opening the oxirane ring of 12,13-epoxydesmycosin dimethylacetal (1) by catalytic hydrogenation gave the 10,11-dihydro-12,13-epoxy derivative (3) as the main product. Reductive oxirane cleavage was accomplished with dissolved metal (Zn) giving the 10,13-dihydro-13-hydroxy compound (6). Mild acid hydrolysis of 6 gave expected 10,13-dihydro-13-hydroxydesmycosin (8), but hydrolysis of 3, under the same conditions, gave three tautomeric desepoxy products.
Naranda
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A
PLIVA Research Institute, Zagreb, Croatia.
Lopotar
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N
Kelnerić
Z
Z
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D015645:Tylosin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
C109712:12,13-epoxydesmycosin; D000900:Anti-Bacterial Agents; C052318:tylosin B; D015645:Tylosin