Abstract
Reactions of 3,11-dioxo fusidane triterpenoids with hydroxylamine in anhydrous ethanol in the presence of a catalytic amount of 4-(dimethylamino)pyridine afforded hydroxyimino derivatives of fusidic acid with high chemo- and stereoselectivity. The products were isolated as pure (3Z,11E) isomers. Their rearrangement by the action of both acid and alkaline agents involved expansion of the A ring or both A and C rings of the triterpene skeleton with the formation of e-lactam moieties as a result of first-order Beckmann rearrangement.
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