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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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
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author Shoemaker, Aaron H
Foker, Elizabeth A
Uttaro, Elena P
Beitel, Sarah K
Griffith, Daniel R
author_facet Shoemaker, Aaron H
Foker, Elizabeth A
Uttaro, Elena P
Beitel, Sarah K
Griffith, Daniel R
author_sort Shoemaker, Aaron H
collection PubMed
description 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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spelling pubmed-106167022023-11-01 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 Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2023-10-23 /pmc/articles/PMC10616702/ /pubmed/37915560 http://dx.doi.org/10.3762/bjoc.19.118 Text en Copyright © 2023, Shoemaker et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Shoemaker, Aaron H
Foker, Elizabeth A
Uttaro, Elena P
Beitel, Sarah K
Griffith, Daniel R
Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions
title Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions
title_full Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions
title_fullStr Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions
title_full_unstemmed Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions
title_short Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions
title_sort synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular heck reactions
topic Full Research Paper
url 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
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