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.
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA. coleman@chemistry.ohio-state.edu
Robert S
RS
Coleman
François-Xavier
FX
Felpin
Wei
W
Chen
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