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

Jordy M. Saya, Thomas R. Roose, Jarryt J. Peek, Bram Weijers, Thomas J.S. de Waal, Christophe M.L. Vande Velde, Romano V.A. Orru, Eelco Ruijter*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

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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.

Original languageEnglish
Pages (from-to)15232-15236
Number of pages5
JournalAngewandte Chemie. International Edition
Volume57
Issue number46
Early online date1 Oct 2018
DOIs
Publication statusPublished - 12 Nov 2018

Funding

We thank Jurriën Collet and Daniel Preschel for HRMS measurements and Elwin Janssen for practical and NMR support (all Vrije Universiteit Amsterdam). We thank the Hercules Foundation (project AUGE/11/029 “3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence”) for funding. This work was financially supported by the Netherlands Organisation for Scientific Research (NWO).

FundersFunder number
Hercules FoundationAUGE/11/029
Nederlandse Organisatie voor Wetenschappelijk Onderzoek

    Keywords

    • Alkaloids
    • cyclization
    • isocyanides
    • natural product synthesis
    • spiroindolines

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