Studies on the Reaction of Mitomycin C with Potassium Ethyl Monothiocarbonate under Reductive Conditions

Article abstract of DOI:10.1021/jo00173a047

Treatment of mitomycin C (1) with the ambident nucleophile potassium ethyl monothiocarbonate (2) under reductive conditions (sodium dithionite) at approximately neutral pH at room temperature led to the formation of equivalent amounts of trans- (17) and cis- (18) aziridine ring-opened disubstituted mitosene adducts.In both cases substitution at carbons 1 and 10 proceeded with sulfur attack.The structural identity of each product was confirmed by high-field 1H and 13C NMR spectral ananlysis as well as by chemical studies.Milder conditions (0-5 deg C) led to the isolation of both trans- (22) and cis- (23) aziridine ring-opened monosubstituted adducts.Compounds 22 and 23 were converted to the corresponding disubstituted products by treatment with additional 2 and sodium dithionite.The implications of these reactions in relation to the mode of action of mitomycin C (1) are discussed.