| Abstract | A 7-step sequence is described for the controlled removal of D-desosamine and L-oleandrose from oleandomycin to give the C3,C5-acetonide 2. A Cope elimination was first used to remove the NMe2 group of desosamine, 3 --> 4. Treatment of 4 with hydroiodic acid gave the iodohydrin 12 with loss of oleandrose, which was followed by removal of the olefinic sugar by hydrolysis with dilute hydrochloric acid to give 14. Acetonide formation and regeneration of the C8 epoxide by mild base then gave 2. The conversion of the C8 epoxide of 4 to the glycols 5 and 6, the enone 7, and the phenylsulphide 8 is also described. |
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