Biomimetic synthesis of galantamine via laccase/TEMPO mediated oxidative coupling. Issue 18 (17th March 2020)

• Record Type: Journal Article
• Authors: Zippilli, Claudio; Botta, Lorenzo; Bizzarri, Bruno Mattia; Baratto, Maria Camilla; Pogni, Rebecca; Saladino, Raffaele
• Is Part Of: RSC advances. Volume 10:Issue 18(2020)
• Page Start: 10897
• Page End: 10903
• Publication Date: 2020-03-17
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0ra00935k
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Laccase-mediated intramolecular oxidative radical coupling of N -formyl-2-bromo- O -methylnorbelladine afforded a novel and isolable spirocyclohexadienonic intermediate of galantamine. 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.