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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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
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author Zippilli, Claudio
Botta, Lorenzo
Bizzarri, Bruno Mattia
Baratto, Maria Camilla
Pogni, Rebecca
Saladino, Raffaele
author_facet Zippilli, Claudio
Botta, Lorenzo
Bizzarri, Bruno Mattia
Baratto, Maria Camilla
Pogni, Rebecca
Saladino, Raffaele
author_sort Zippilli, Claudio
collection PubMed
description 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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spelling pubmed-90504312022-04-29 Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling Zippilli, Claudio Botta, Lorenzo Bizzarri, Bruno Mattia Baratto, Maria Camilla Pogni, Rebecca Saladino, Raffaele RSC Adv Chemistry 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. The Royal Society of Chemistry 2020-03-17 /pmc/articles/PMC9050431/ /pubmed/35492924 http://dx.doi.org/10.1039/d0ra00935k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Zippilli, Claudio
Botta, Lorenzo
Bizzarri, Bruno Mattia
Baratto, Maria Camilla
Pogni, Rebecca
Saladino, Raffaele
Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling
title Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling
title_full Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling
title_fullStr Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling
title_full_unstemmed Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling
title_short Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling
title_sort biomimetic synthesis of galantamine via laccase/tempo mediated oxidative coupling
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9050431/
https://www.ncbi.nlm.nih.gov/pubmed/35492924
http://dx.doi.org/10.1039/d0ra00935k
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