Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Pollok, Dennis, Großmann, Luca M., Behrendt, Torsten, Opatz, Till, Waldvogel, Siegfried R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
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
_version_ 1784804396013453312
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
work_keys_str_mv AT pollokdennis ageneralelectrosynthesisapproachtoamaryllidaceaealkaloids
AT großmannlucam ageneralelectrosynthesisapproachtoamaryllidaceaealkaloids
AT behrendttorsten ageneralelectrosynthesisapproachtoamaryllidaceaealkaloids
AT opatztill ageneralelectrosynthesisapproachtoamaryllidaceaealkaloids
AT waldvogelsiegfriedr ageneralelectrosynthesisapproachtoamaryllidaceaealkaloids
AT pollokdennis generalelectrosynthesisapproachtoamaryllidaceaealkaloids
AT großmannlucam generalelectrosynthesisapproachtoamaryllidaceaealkaloids
AT behrendttorsten generalelectrosynthesisapproachtoamaryllidaceaealkaloids
AT opatztill generalelectrosynthesisapproachtoamaryllidaceaealkaloids
AT waldvogelsiegfriedr generalelectrosynthesisapproachtoamaryllidaceaealkaloids