Iodospirocyclization of Tryptamine‐Derived Isocyanides: Formal Total Synthesis of Aspidofractinine. (17th October 2018)

• Record Type: Journal Article
• Authors: Saya, Jordy M.; Roose, Thomas R.; Peek, Jarryt J.; Weijers, Bram; de Waal, Thomas J. S.; Vande Velde, Christophe M. L.; Orru, Romano V. A.; Ruijter, Eelco
• Is Part Of: Angewandte Chemie. Volume 130:Number 46(2018)
• Page Start: 15452
• Page End: 15456
• Publication Date: 2018-10-17
• Subjects: Alkaloide -- Cyclisierungen -- Isocyanide -- Naturstoffsynthesen -- Spiroindoline; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201809678
• Languages: English
• ISSNs: 0044-8249

Abstract

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.