Mitomycin synthetic studies: stereocontrolled and convergent synthesis of a fully elaborated aziridinomitosane.
Full details of a stereocontrolled and convergent synthetic route to 9a-desmethoxymitomycin A (1) are reported. The target molecule possesses the parent tetrahydropyrrolo[1,2-a]indole ring system characteristic of the mitomycin family of antitumor agents. The synthesis was based on the diastereocontrolled addition of a fully elaborated cinnamylstannane to a pyrrolidine-based N-acyliminium ion as the key convergent step, which resulted in the installation of the C9 and C9a stereogenic centers.
Coleman
Robert S
RS
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA. coleman@chemistry.ohio-state.edu
Felpin
François-Xavier
FX
Chen
Wei
W
D001388:Aziridines / Q000138:chemical synthesis*; D003500:Cyclization; D016685:Mitomycin / Q000138:chemical synthesis*; D008937:Mitomycins / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D001388:Aziridines; D008937:Mitomycins; C494068:desmethoxymitomycin A; C435767:mitosane; D016685:Mitomycin