Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η(4)-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...

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Detalles Bibliográficos
Autores principales: Shoemaker, Aaron H, Foker, Elizabeth A, Uttaro, Elena P, Beitel, Sarah K, Griffith, Daniel R
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10616702/
https://www.ncbi.nlm.nih.gov/pubmed/37915560
http://dx.doi.org/10.3762/bjoc.19.118
Descripción
Sumario:The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η(4)-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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