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

Research output: Contribution to JournalArticleAcademicpeer-review

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
JournalAngewandte Chemie - International Edition
Volume57
Issue number46
Early online date1 Oct 2018
DOIs
Publication statusPublished - 12 Nov 2018

Fingerprint

Imines
Cyanides
Iodides
aspidofractinine
tryptamine
N-iodosuccinimide

Keywords

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

Cite this

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. / Iodospirocyclization of Tryptamine-Derived Isocyanides : Formal Total Synthesis of Aspidofractinine. In: Angewandte Chemie - International Edition. 2018 ; Vol. 57, No. 46. pp. 15232-15236.
@article{88554b6da5ee4c3b9e0091e9f67224ff,
title = "Iodospirocyclization of Tryptamine-Derived Isocyanides: Formal Total Synthesis of Aspidofractinine",
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.",
keywords = "Alkaloids, cyclization, isocyanides, natural product synthesis, spiroindolines",
author = "Saya, {Jordy M.} and Roose, {Thomas R.} and Peek, {Jarryt J.} and Bram Weijers and {de Waal}, {Thomas J.S.} and {Vande Velde}, {Christophe M.L.} and Orru, {Romano V.A.} and Eelco Ruijter",
year = "2018",
month = "11",
day = "12",
doi = "10.1002/anie.201809678",
language = "English",
volume = "57",
pages = "15232--15236",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "Wiley",
number = "46",

}

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

In: Angewandte Chemie - International Edition, Vol. 57, No. 46, 12.11.2018, p. 15232-15236.

Research output: Contribution to JournalArticleAcademicpeer-review

TY - JOUR

T1 - Iodospirocyclization of Tryptamine-Derived Isocyanides

T2 - Formal Total Synthesis of Aspidofractinine

AU - Saya, Jordy M.

AU - Roose, Thomas R.

AU - Peek, Jarryt J.

AU - Weijers, Bram

AU - de Waal, Thomas J.S.

AU - Vande Velde, Christophe M.L.

AU - Orru, Romano V.A.

AU - Ruijter, Eelco

PY - 2018/11/12

Y1 - 2018/11/12

N2 - 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.

AB - 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.

KW - Alkaloids

KW - cyclization

KW - isocyanides

KW - natural product synthesis

KW - spiroindolines

UR - http://www.scopus.com/inward/record.url?scp=85055118814&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85055118814&partnerID=8YFLogxK

U2 - 10.1002/anie.201809678

DO - 10.1002/anie.201809678

M3 - Article

VL - 57

SP - 15232

EP - 15236

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 46

ER -