Synthesis of N-substituted 10-des(carbamoyloxy)-10-azidomitomycins

Article abstract of DOI:10.1055/s-1997-1297

A general method for the synthesis of N-substituted 10-des(carbamoyloxy)-10-azidomitomycins 5 has been developed. These compounds are expected to be rapidly converted to the corresponding C-10 isothiocyanate derivatives allowing mitomycins to couple to biomolecules. The key synthetic intermediate was 10-des(carbamoyloxy)-10-azidomitomycin C (12). Compound 12 was prepared by decarbamoylation of mitomycin C (1) followed by aziridine protection with Fmoc-chloride and activation of the C-10 site with methanesulfonyl chloride. Deprotection of the Fmoc unit with morpholine and treatment with NaN₃ gave 12.