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A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids
Amaryllidaceae alkaloids appeal to organic chemists with their attractive structures and their impressive antitumor and acetylcholinesterase inhibitory properties. We demonstrate a highly versatile access to this family of natural products. A general protocol with high yields in a sustainable electr...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9543536/ https://www.ncbi.nlm.nih.gov/pubmed/35662286 http://dx.doi.org/10.1002/chem.202201523 |
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author | Pollok, Dennis Großmann, Luca M. Behrendt, Torsten Opatz, Till Waldvogel, Siegfried R. |
author_facet | Pollok, Dennis Großmann, Luca M. Behrendt, Torsten Opatz, Till Waldvogel, Siegfried R. |
author_sort | Pollok, Dennis |
collection | PubMed |
description | Amaryllidaceae alkaloids appeal to organic chemists with their attractive structures and their impressive antitumor and acetylcholinesterase inhibitory properties. We demonstrate a highly versatile access to this family of natural products. A general protocol with high yields in a sustainable electro‐organic key transformation on a metal‐free anode to spirodienones facilitates functionalization to the alkaloids. The biomimetic syntheses start with the readily available, inexpensive biogenic starting materials methyl gallate, O‐methyl tyramine, and vanillin derivatives. Through known dynamic resolutions, this technology provides access to both enantiomeric series of (epi‐)martidine, (epi‐)crinine, siculine, and galantamine, clinically prescribed for the treatment of Alzheimer's disease. |
format | Online Article Text |
id | pubmed-9543536 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-95435362022-10-14 A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids Pollok, Dennis Großmann, Luca M. Behrendt, Torsten Opatz, Till Waldvogel, Siegfried R. Chemistry Research Articles Amaryllidaceae alkaloids appeal to organic chemists with their attractive structures and their impressive antitumor and acetylcholinesterase inhibitory properties. We demonstrate a highly versatile access to this family of natural products. A general protocol with high yields in a sustainable electro‐organic key transformation on a metal‐free anode to spirodienones facilitates functionalization to the alkaloids. The biomimetic syntheses start with the readily available, inexpensive biogenic starting materials methyl gallate, O‐methyl tyramine, and vanillin derivatives. Through known dynamic resolutions, this technology provides access to both enantiomeric series of (epi‐)martidine, (epi‐)crinine, siculine, and galantamine, clinically prescribed for the treatment of Alzheimer's disease. John Wiley and Sons Inc. 2022-07-13 2022-09-06 /pmc/articles/PMC9543536/ /pubmed/35662286 http://dx.doi.org/10.1002/chem.202201523 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Research Articles Pollok, Dennis Großmann, Luca M. Behrendt, Torsten Opatz, Till Waldvogel, Siegfried R. A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids |
title | A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids |
title_full | A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids |
title_fullStr | A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids |
title_full_unstemmed | A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids |
title_short | A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids |
title_sort | general electro‐synthesis approach to amaryllidaceae alkaloids |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9543536/ https://www.ncbi.nlm.nih.gov/pubmed/35662286 http://dx.doi.org/10.1002/chem.202201523 |
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