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Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy
Aetokthonotoxin has recently been identified as the cyanobacterial neurotoxin causing Vacuolar Myelinopathy, a fatal neurologic disease, spreading through a trophic cascade and affecting birds of prey such as the bald eagle in the USA. Here, we describe the total synthesis of this specialized metabo...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8453946/ https://www.ncbi.nlm.nih.gov/pubmed/34081364 http://dx.doi.org/10.1002/chem.202101848 |
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author | Ricardo, Manuel G. Schwark, Markus Llanes, Dayma Niedermeyer, Timo H. J. Westermann, Bernhard |
author_facet | Ricardo, Manuel G. Schwark, Markus Llanes, Dayma Niedermeyer, Timo H. J. Westermann, Bernhard |
author_sort | Ricardo, Manuel G. |
collection | PubMed |
description | Aetokthonotoxin has recently been identified as the cyanobacterial neurotoxin causing Vacuolar Myelinopathy, a fatal neurologic disease, spreading through a trophic cascade and affecting birds of prey such as the bald eagle in the USA. Here, we describe the total synthesis of this specialized metabolite. The complex, highly brominated 1,2’‐biindole could be synthesized via a Somei‐type Michael reaction as key step. The optimised sequence yielded the natural product in five steps with an overall yield of 29 %. |
format | Online Article Text |
id | pubmed-8453946 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-84539462021-09-27 Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy Ricardo, Manuel G. Schwark, Markus Llanes, Dayma Niedermeyer, Timo H. J. Westermann, Bernhard Chemistry Communications Aetokthonotoxin has recently been identified as the cyanobacterial neurotoxin causing Vacuolar Myelinopathy, a fatal neurologic disease, spreading through a trophic cascade and affecting birds of prey such as the bald eagle in the USA. Here, we describe the total synthesis of this specialized metabolite. The complex, highly brominated 1,2’‐biindole could be synthesized via a Somei‐type Michael reaction as key step. The optimised sequence yielded the natural product in five steps with an overall yield of 29 %. John Wiley and Sons Inc. 2021-06-18 2021-08-19 /pmc/articles/PMC8453946/ /pubmed/34081364 http://dx.doi.org/10.1002/chem.202101848 Text en © 2021 The Authors. Published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Ricardo, Manuel G. Schwark, Markus Llanes, Dayma Niedermeyer, Timo H. J. Westermann, Bernhard Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy |
title | Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy |
title_full | Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy |
title_fullStr | Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy |
title_full_unstemmed | Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy |
title_short | Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy |
title_sort | total synthesis of aetokthonotoxin, the cyanobacterial neurotoxin causing vacuolar myelinopathy |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8453946/ https://www.ncbi.nlm.nih.gov/pubmed/34081364 http://dx.doi.org/10.1002/chem.202101848 |
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