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Iodospirocyclization of Tryptamine-Derived Isocyanides: Formal Total Synthesis of Aspidofractinine
Jordy M Saya1, Thomas R Roose1, Jarryt J Peek1
1Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081, HZ, Amsterdam, The Netherlands.
Abstract:
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.
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