Synthesis of xanthohumol and xanthohumol-d3 from naringenin. Issue 46 (31st August 2021)

• Record Type: Journal Article
• Authors: Andrusiak, Joanna; Mylkie, Kinga; Wysocka, Małgorzata; Ścianowski, Jacek; Wolan, Andrzej; Budny, Marcin
• Is Part Of: RSC advances. Volume 11:Issue 46(2021)
• Page Start: 28934
• Page End: 28939
• Publication Date: 2021-08-31
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1ra05443k
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A six-step synthesis of xanthohumol and its d3 -derivative from easily accessible naringenin is reported. Abstract : A six-step synthesis of xanthohumol (1a ) and its d3 -derivative (1b ) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an α, β-conjugated ketone system. Compound 1b was used as an internal standard in stable isotope dilution assays of 1a in two Polish beers.