Facile and scalable synthesis of baphicacanthin A by a two-pot procedure. Issue 9 (3rd May 2023)

• Record Type: Journal Article
• Authors: Cuan, Yalong; Li, Wenhao; Dou, Yingchao; Yang, Guanyu
• Is Part Of: Natural product research. Volume 37:Issue 9(2023)
• Page Start: 1439
• Page End: 1443
• Publication Date: 2023-05-03
• Subjects: Baphicacanthin A -- phenoxazinone -- total synthesis -- aerobic oxidation -- cross-cyclocondensation; Short communication; Natural products -- Periodicals; Natural products -- Research -- Periodicals; Biological Factors -- Periodicals; Biological Products -- Periodicals; 547
• DOI: 10.1080/14786419.2021.2011275
• Languages: English
• ISSNs: 1478-6419

Abstract

Abstract: Facile two-pot total synthesis of baphicacanthin A, a natural phenoxazinone alkaloid isolated from the roots of Baphicacanthus cusia which has been utilized as a traditional chinese medicine to effectively treat disease caused by coronavirus, has been developed from simple and commercially available starting materials. Catalytic aerobic oxidative cross-cyclocondensation of equimolar 2-aminophenol and 3-methoxy-2-hydroxylphenol in water was used to construct the key molecular skeleton 2-hydroxy-3 H -phenoxazin-3-one. Gram scale synthesis was realized in 80% overall yield with practical convenience. Graphical Abstract: UF0001