Issue 18, 2020
From the journal:

RSC Advances

Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling†

Claudio Zippilli,a   Lorenzo Botta,a   Bruno Mattia Bizzarri,a   Maria Camilla Baratto,b   Rebecca Pognib  and  Raffaele Saladino ORCID logo *a  

* Corresponding authors

a Department of Ecological and Biological Sciences, University of Tuscia, Via S. C. De Lellis 44, Viterbo, Italy
E-mail: saladino@unitus.it

b Department of Biotechnology, Chemistry and Pharmacy, University of Siena, Via Aldo Moro 2, 53100 Siena, Italy

Abstract

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.

Graphical abstract: Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling

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Article information

DOI
https://doi.org/10.1039/D0RA00935K
Article type
Paper
Submitted
31 Jan 2020
Accepted
05 Mar 2020
First published
17 Mar 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 10897-10903

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Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling

C. Zippilli, L. Botta, B. M. Bizzarri, M. C. Baratto, R. Pogni and R. Saladino, RSC Adv., 2020, 10, 10897 DOI: 10.1039/D0RA00935K

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