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Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling†
Claudio Zippilli,Lorenzo Botta,Bruno Mattia Bizzarri,Maria Camilla Baratto,Rebecca Pogni,Raffaele Saladino
RSC Advances Pub Date : 03/17/2020 00:00:00 , DOI:10.1039/D0RA00935K
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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