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IBX-mediated oxidative addition of isocyanides to cyclic secondary amines: total syntheses of alangiobussine and alangiobussinine

Abstract

Present study describes a robust and general method for the synthesis of C(1)-carboxamides through IBX-mediated oxidative addition of isocyanides to the tryptolines and 1,2,3,4-tetrahydroisoquinolines. In this transformation, IBX plays a dual role of oxidant as well as Lewis acid to activate the imine facilitating the isocyanide addition. Detailed mechanistic investigations were performed by isotopic labeling and real-time NMR experiments. The method was utilized for the gram scale syntheses of two alkaloids alangiobussine and alangiobussinine in 63 % and 45 % overall yield respectively.

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Publication details

The article was received on 08 Jul 2019, accepted on 13 Aug 2019 and first published on 14 Aug 2019


Article type: Communication
DOI: 10.1039/C9CC05215A
Chem. Commun., 2019, Accepted Manuscript

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    IBX-mediated oxidative addition of isocyanides to cyclic secondary amines: total syntheses of alangiobussine and alangiobussinine

    M. Ambule, S. Tripathi, A. Ghoshal and A. K. Srivastava, Chem. Commun., 2019, Accepted Manuscript , DOI: 10.1039/C9CC05215A

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