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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...

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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
Descripción
Sumario: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.