A General Electro-Synthesis Approach to Amaryllidaceae Alkaloids.
alkaloid
amaryllidaceae
biomimetic
electrosynthesis
galantamine
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
06 Sep 2022
06 Sep 2022
Historique:
received:
17
05
2022
pubmed:
7
6
2022
medline:
8
9
2022
entrez:
6
6
2022
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 35662286
doi: 10.1002/chem.202201523
pmc: PMC9543536
doi:
Substances chimiques
Alkaloids
0
Amaryllidaceae Alkaloids
0
Cholinesterase Inhibitors
0
Plant Extracts
0
Acetylcholinesterase
EC 3.1.1.7
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202201523Subventions
Organisme : Forschungsinitiative Rheinland-Pfalz
ID : SusInnoScience
Organisme : Rhineland-Palatinate Natural Products Research Centre, Johannes Gutenberg-Universität Mainz
Organisme : Verband der Chemischen Industrie
Informations de copyright
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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