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Mitomycin Synthetic Studies:  Stereocontrolled and Convergent Synthesis of a Fully Elaborated Aziridinomitosane

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journal contribution
posted on 15.10.2004 by Robert S. Coleman, François-Xavier Felpin, Wei Chen
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.