Iodospirocyclization of Tryptamine-Derived Isocyanides: Formal Total Synthesis of Aspidofractinine.

Iodospirocyclization of Tryptamine-Derived Isocyanides: Formal Total Synthesis of Aspidofractinine.
Angew Chem Int Ed Engl. 2018 Oct 01;:
Authors: Saya JM, Roose TR, Peek JJ, Weijers B, de Waal TJS, Vande Velde CML, Orru RVA, Ruijter E
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.
PMID: 30273989 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - October 1, 2018 Category: Chemistry Authors: Saya JM, Roose TR, Peek JJ, Weijers B, de Waal TJS, Vande Velde CML, Orru RVA, Ruijter E Tags: Angew Chem Int Ed Engl Source Type: research