Your browser doesn't support javascript.
loading
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.
Afiliación
  • Saya JM; Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081, HZ, Amsterdam, The Netherlands.
  • Roose TR; Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081, HZ, Amsterdam, The Netherlands.
  • Peek JJ; Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081, HZ, Amsterdam, The Netherlands.
  • Weijers B; Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081, HZ, Amsterdam, The Netherlands.
  • de Waal TJS; Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081, HZ, Amsterdam, The Netherlands.
  • Vande Velde CML; Faculty of Applied Engineering, Advanced Reactor Technology, University of Antwerp, Groenenborgerlaan 171, 2020, Antwerpen, Belgium.
  • Orru RVA; Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081, HZ, Amsterdam, The Netherlands.
  • Ruijter E; Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081, HZ, Amsterdam, The Netherlands.
Angew Chem Int Ed Engl ; 57(46): 15232-15236, 2018 11 12.
Article en En | MEDLINE | ID: mdl-30273989
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.
Palabras clave
Texto completo
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2018 Tipo del documento: Article País de afiliación: Países Bajos
Texto completo
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2018 Tipo del documento: Article País de afiliación: Países Bajos