6-Demethyl-6-halo- and 6-Demethyl-6-thiomitomycins: Synthesis of Novel Mitomycin Derivatives Involving a Tandem Michael Addition/Retro-Mannich Reaction Sequence

Article abstract of DOI:10.1021/jo00084a028

Synthesis of novel 6-demethyl-6-halomitomycins (3, 4, 6, and 7) and 6-demethyl-6-thiomytomycins (5 and 8) is described from key intermediates, namely, 6-demethyl-7,7-(ethylenedioxy)-6,6-dihalo-6,7-dihydromitosanes (18 and 19) and 6-demethyl-7,7-(ethylenedioxy)-6,7-dihydro-6-thiomitosane (20), respectively.Compounds 18-20 were prepared through a tandem Michael addition and a retro-Mannich reaction sequence (N-halosucinimide or cationic arylsulfenyl species in the presence of Et2NH) on 10.