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Authors: Pollok, Dennis
Großmann, Luca M.
Behrendt, Torsten
Opatz, Till
Waldvogel, Siegfried R.
Title: A general electro-synthesis approach to amaryllidaceae alkaloids
Online publication date: 2-Feb-2023
Year of first publication: 2022
Language: english
Abstract: 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.
DDC: 540 Chemie
540 Chemistry and allied sciences
Institution: Johannes Gutenberg-Universität Mainz
Department: FB 09 Chemie, Pharmazie u. Geowissensch.
Place: Mainz
Version: Published version
Publication type: Zeitschriftenaufsatz
Document type specification: Scientific article
License: CC BY-NC-ND
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Journal: Chemistry - a European journal
Pages or article number: 202201523
Publisher: John Wiley & Sons, Ltd
Publisher place: Weinheim
Issue date: 2022
ISSN: 1521-3765
Publisher DOI: 10.1002/chem.202201523
Appears in collections:DFG-491381577-H

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