Alkylation of 4-(demethoxy)daunorubicin (I) with 2-bromoethanol (II) affords the hydroxyethyl amine (III). This is treated with methanesulfonyl chloride and diisopropyl ethylamine to produce the bis-mesylate (IV). Cyclization of (IV) to the title aziridino derivative is then accomplished by treatment with silicagel or with diisopropyl ethylamine.
The title aziridine derivative was prepared by treatment of the known 4-demethoxy-N-(2-hydroxyethyl)-4'-O-metanesulfonyldaunorubicin (I) with silica gel in a dichloromethane/methanol solution.