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Iodospirocyclization of tryptamine‐derived isocyanides

Journal Contribution - Journal Article

Subtitle:formal total synthesis of aspidofractinine
The N‐iodosuccinimide‐mediated spirocyclization of tryptamine‐derived isocyanides to generate spiroindolenines is reported. The products contain both an imine and an imidoyl iodide as flexible handles for follow‐up chemistry. Nucleophilic addition typically occurs chemoselectively on the imine moiety with complete diastereoselectivity, providing opportunities for the construction of complex molecular frameworks. The synthetic potential of the method was showcased in the formal total synthesis of (±)‐aspidofractinine.
Journal: Angewandte Chemie International Edition
ISSN: 1433-7851
Volume: 57
Pages: 15232 - 15236
Publication year:2018