Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds

BACKGROUND: Tandem olefin metathesis sequences are known to be versatile for the generation of natural product scaffolds and have also been used for ring opening of strained carbo- and heterocycles. In this paper we demonstrate the potential of these reactions for the desymmetrization of 7-azabicycl...

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Detalles Bibliográficos
Autores principales: Maison, Wolfgang, Büchert, Marina, Deppermann, Nina
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2007
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2200670/
https://www.ncbi.nlm.nih.gov/pubmed/18088413
http://dx.doi.org/10.1186/1860-5397-3-48
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author Maison, Wolfgang
Büchert, Marina
Deppermann, Nina
author_facet Maison, Wolfgang
Büchert, Marina
Deppermann, Nina
author_sort Maison, Wolfgang
collection PubMed
description BACKGROUND: Tandem olefin metathesis sequences are known to be versatile for the generation of natural product scaffolds and have also been used for ring opening of strained carbo- and heterocycles. In this paper we demonstrate the potential of these reactions for the desymmetrization of 7-azabicycloalkenes. RESULTS: We have established efficient protocols for the desymmetrization of different 7-azabicycloalkenes by intra- and intermolecular tandem metathesis sequences with ruthenium based catalysts. CONCLUSION: Desymmetrization of 7-azabicycloalkenes by olefin metathesis is an efficient process for the preparation of common natural product scaffolds such as pyrrolidines, indolizidines and isoindoles.
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spelling pubmed-22006702008-01-16 Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds Maison, Wolfgang Büchert, Marina Deppermann, Nina Beilstein J Org Chem Full Research Paper BACKGROUND: Tandem olefin metathesis sequences are known to be versatile for the generation of natural product scaffolds and have also been used for ring opening of strained carbo- and heterocycles. In this paper we demonstrate the potential of these reactions for the desymmetrization of 7-azabicycloalkenes. RESULTS: We have established efficient protocols for the desymmetrization of different 7-azabicycloalkenes by intra- and intermolecular tandem metathesis sequences with ruthenium based catalysts. CONCLUSION: Desymmetrization of 7-azabicycloalkenes by olefin metathesis is an efficient process for the preparation of common natural product scaffolds such as pyrrolidines, indolizidines and isoindoles. Beilstein-Institut 2007-12-18 /pmc/articles/PMC2200670/ /pubmed/18088413 http://dx.doi.org/10.1186/1860-5397-3-48 Text en Copyright © 2007, Maison et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Maison, Wolfgang
Büchert, Marina
Deppermann, Nina
Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds
title Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds
title_full Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds
title_fullStr Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds
title_full_unstemmed Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds
title_short Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds
title_sort desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2200670/
https://www.ncbi.nlm.nih.gov/pubmed/18088413
http://dx.doi.org/10.1186/1860-5397-3-48
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