New dihydro and tetrahydro derivatives of desmycosin. III. The opening of oxirane ring of 12,13-epoxydesmycosin

Article abstract of DOI:10.7164/antibiotics.50.860

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.