IBX-mediated oxidative addition of isocyanides to cyclic secondary amines: total syntheses of alangiobussine and alangiobussinine.
Chem Commun (Camb)
; 55(73): 10872-10875, 2019 Sep 10.
Article
em En
| MEDLINE
| ID: mdl-31433406
ABSTRACT
The present study describes a robust and general method for the synthesis of C(1)-carboxamides through IBX-mediated oxidative addition of isocyanides to tryptolines and 1,2,3,4-tetrahydroisoquinolines. In this transformation, IBX plays a dual role of an oxidant and Lewis acid to activate imine facilitating 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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MEDLINE
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En
Ano de publicação:
2019
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Article