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.
Zippilli, C., Botta, L., Bizzarri, B.M., Baratto, M.C., Pogni, R., Saladino, R. (2020). Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling. RSC ADVANCES, 10, 10897-10903 [10.1039/d0ra00935k].
Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling
Lorenzo Botta;Bruno Mattia Bizzarri;Maria Camilla Baratto;Rebecca Pogni;
2020-01-01
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
https://hdl.handle.net/11365/1107292
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