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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...

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Autores principales: Ricardo, Manuel G., Schwark, Markus, Llanes, Dayma, Niedermeyer, Timo H. J., Westermann, Bernhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
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 %.
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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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