Iodospirocyclization of tryptamine‐derived isocyanides

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.

Publication year:2018

Keywords:A1 Journal article

BOF-keylabel:yes

BOF-publication weight:6

CSS-citation score:2

Authors:International

Authors from:Higher Education

Accessibility:Open