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The macrolide antibiotic, picromycin, was found to be synthesized from narbonolide by the following two metabolic pathways: (A) Narbonolide (I) → narbomycin (II) → picromycin (III). (B) Narbonolide (I) → picronolide (IV) → picromycin (III). In path (A) glycosidation at C-5 with desosamine preceded hydroxylation at C-12, while in path (B) the reverse is true.
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Maezawa et al. (1973) studied this question.
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