Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy

An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key intermediate for the synthesis of (−)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)...

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Detalles Bibliográficos
Autores principales: Shigeoka, Daisuke, Kamon, Takuma, Yoshimitsu, Takehiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3678661/
https://www.ncbi.nlm.nih.gov/pubmed/23766801
http://dx.doi.org/10.3762/bjoc.9.99
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author Shigeoka, Daisuke
Kamon, Takuma
Yoshimitsu, Takehiko
author_facet Shigeoka, Daisuke
Kamon, Takuma
Yoshimitsu, Takehiko
author_sort Shigeoka, Daisuke
collection PubMed
description An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key intermediate for the synthesis of (−)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N–iron intermediates in the redox states were operative.
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spelling pubmed-36786612013-06-13 Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy Shigeoka, Daisuke Kamon, Takuma Yoshimitsu, Takehiko Beilstein J Org Chem Full Research Paper An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key intermediate for the synthesis of (−)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N–iron intermediates in the redox states were operative. Beilstein-Institut 2013-05-03 /pmc/articles/PMC3678661/ /pubmed/23766801 http://dx.doi.org/10.3762/bjoc.9.99 Text en Copyright © 2013, Shigeoka 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
Shigeoka, Daisuke
Kamon, Takuma
Yoshimitsu, Takehiko
Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy
title Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy
title_full Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy
title_fullStr Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy
title_full_unstemmed Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy
title_short Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy
title_sort formal synthesis of (−)-agelastatin a: an iron(ii)-mediated cyclization strategy
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3678661/
https://www.ncbi.nlm.nih.gov/pubmed/23766801
http://dx.doi.org/10.3762/bjoc.9.99
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