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A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
- Aksenov, Nicolai A., Aksenov, Alexander V., Kornienko, Alexander, De Carvalho, Annelise, Mathieu, Véronique, Aksenov, Dmitrii A., Ovcharov, Sergei N., Griaznov, Georgii D., Rubin, Michael
- RSC advances 2018 v.8 no.64 pp. 36980-36986
- alkaloids, antineoplastic activity, chemical bonding, nitroalkanes, solvents
- A second generation polyphosphoric acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C–C and C–N bonds and ring C assembly. This modification allows the elimination of unnecessary solvent change operations and all steps are carried out in a true, uninterrupted one-pot manner. A further improvement involves the possibility to install an ortho-amino group in situ. A synthetic application of this method is showcased by the concise synthesis of an isocryptolepine alkaloid and its synthetic analogs with potent anticancer activities.