Transformation of 3-0-mycarosylerythronolide B, an intermediate of erythromycin biogenesis, into 3-0-mycarosyl-(8S)-8-fluoroerythronolide B using trifluoromethyl hypofluorite

Add time:08/02/2019    Source:sciencedirect.com

Treatment of 3-0-mycarosylerythronolide B (V) with glacial acetic acid gave 3-0-mycarosyl-8,9-anhydroerythronolide B 6,9-hemiketal (VI) together with 3-0-mycarosylerythronolide B 6,9; 9,11-spiroketal (VII). Fluorination of VI with trifluoromethyl hypofluorite (CF3OF) gave a mixture of 3-0-mycarosyl-(8S)-8-fluoroerythronolide B (IX) and 3-0-mycarosyl-(8S)-8-fluoroerythronolide B 6,9;9,11-spiroketal (X) (major product).

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