Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1391005 | Carbohydrate Research | 2006 | 7 Pages |
Abstract
Three naturally occurring di-C-glycosylflavonoids, phloretin (dihydrochalcone), naringenin (flavanone), and apigenin (flavone) bis-6,8-C-β-d-glucopyranosides (4, 5, and 6), were synthesized in total yields of 52.3%, 53.5%, and 36.4%, respectively, starting from the key compound, di-C-β-d-glucopyranosylphloroacetophenone (1). Benzyl protection of the phenolic hydroxyls in 1 and a subsequent aldol condensation with benzyloxybenzaldehyde led to the production of chalcone 3, which, after hydrogenolysis or acid hydrolysis and deprotection, gave 4 and 5, respectively. The acetylation of 5, followed by DDQ oxidation and deprotection, gave 6.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Shingo Sato, Toshiki Akiya, Hiroaki Nishizawa, Toshiyuki Suzuki,