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Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions.
Shoemaker, Aaron H; Foker, Elizabeth A; Uttaro, Elena P; Beitel, Sarah K; Griffith, Daniel R.
Afiliación
  • Shoemaker AH; Department of Chemistry, Lafayette College, 730 High St., Easton, PA 18042, USA.
  • Foker EA; Department of Chemistry, Lafayette College, 730 High St., Easton, PA 18042, USA.
  • Uttaro EP; Department of Chemistry, Lafayette College, 730 High St., Easton, PA 18042, USA.
  • Beitel SK; Department of Chemistry, Lafayette College, 730 High St., Easton, PA 18042, USA.
  • Griffith DR; Department of Chemistry, Lafayette College, 730 High St., Easton, PA 18042, USA.
Beilstein J Org Chem ; 19: 1615-1619, 2023.
Article en En | MEDLINE | ID: mdl-37915560
ABSTRACT
The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of

steps:

1) nucleophilic amine addition and subsequent Boc-protection, 2) photochemical demetallation of the iron complex, and 3) an intramolecular Heck reaction. Minor modifications to the protocol enabled access to the related 2-azabicyclo[4.4.1]undecane system, albeit in lower yield.
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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Idioma: En Revista: Beilstein J Org Chem Año: 2023 Tipo del documento: Article País de afiliación: Estados Unidos
Texto completo
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Idioma: En Revista: Beilstein J Org Chem Año: 2023 Tipo del documento: Article País de afiliación: Estados Unidos