Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling

Laccase-mediated intramolecular oxidative radical coupling of N-formyl-2-bromo-O-methylnorbelladine afforded a novel and isolable spirocyclohexadienonic intermediate of galantamine. High yield and conversion of substrate were obtained in the presence of the redox mediator 2,2,6,6-tetramethylpiperidi...

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Detalles Bibliográficos
Autores principales: Zippilli, Claudio, Botta, Lorenzo, Bizzarri, Bruno Mattia, Baratto, Maria Camilla, Pogni, Rebecca, Saladino, Raffaele
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9050431/
https://www.ncbi.nlm.nih.gov/pubmed/35492924
http://dx.doi.org/10.1039/d0ra00935k
Descripción
Sumario:Laccase-mediated intramolecular oxidative radical coupling of N-formyl-2-bromo-O-methylnorbelladine afforded a novel and isolable spirocyclohexadienonic intermediate of galantamine. High yield and conversion of substrate were obtained in the presence of the redox mediator 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). This laccase procedure, with an overall yield of 34%, represents a scalable and environmentally friendly alternative to previously reported syntheses of galantamine based on the use of potassium ferricyanide as an unspecific radical coupling reagent.

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