Mitomycin synthetic studies: Stereocontrolled and convergent synthesis of a fully elaborated aziridinomitosane

RS Coleman, FX Felpin, W Chen

Index: Coleman, Robert S.; Felpin, Francois-Xavier; Chen, Wei Journal of Organic Chemistry, 2004 , vol. 69, # 21 p. 7309 - 7316

Full Text: HTML

Citation Number: 36

Abstract

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 ...