A convergent approach to the mitomycin ring system.
[structure: see text]. A novel stereoselective approach to the ring system of the mitomycins is described. The synthesis was based on a convergent strategy involving a stereocontrolled addition of a beta-phenyl silyl enol ether to a pyrroline N-acyliminium ion followed by an intramolecular palladium-catalyzed aryl triflate amination to afford the (9R*,9aR*)-tetrahydropyrrolo[1,2-a]indole ring system.
Coleman
R S
RS
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210-1185, USA. coleman@chemistry.ohio-state.edu
Chen
W
W
D000477:Alkylating Agents / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D016685:Mitomycin / Q000138:chemical synthesis* / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D011758:Pyrroles / Q000737:chemistry*
D000477:Alkylating Agents; D011758:Pyrroles; C013231:pyrroline; D016685:Mitomycin