Semisynthetic macrolidic antibiotics, microbiological...

Details Semisynthetic macrolidic antibiotics, microbiological... Semisynthetic macrolidic antibiotics, microbiological...

C - Chemistry, Metallurgy

07

D

260/355.1, 260/2

C07D 313/00 (2006.01) C07H 17/08 (2006.01)

Patent

CA 1189856

ABSTRACT OF THE DISCLOSURE A derivative of erythronolide A, namely (8S)-8- fluoroerythronolide A, a derivative of erythronolide B, namely (8S)-fluoroerythronolide B, or a derivative of 3-0- mycarsolyerythronolide B, namely 3-0-mycarsoyl-(8S)-fluoro- erythronolide B, which are useful as substrates in the pre- paration of the corresponding (8S)-8-fluoro derivatives of the exythromycins A, B, C and D, as well as 3-0-oleandrosyl- 5-desosaminyl-(8S)-8-fluoroerythronolide A and 3-0-oleandrosyl- 5-0-desosaminyl-(8S)-8-fluoroerythronolide B, all belonging to the class of the macrolide antibiotics by fermantation carried out with mutants blocked in the synthesis respec- tively of erythromycin and of oleandomycin, namely Streptomyces erythreus ATCC 31772 and Streptomyces anticio- ticus ATCC 31771. The preparation of the aforesaid substrate comprises the conversion of erythronolide A, erythronolide B or 3-0-mycarsoyl-exythronolide B into the corresponding he?i- acetal, the reaction of the latter with a compound capable of generating eletrophilic fluorine and the opening of the resulting acetal with aqueous acid.

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