title: The first total synthesis of 7-O-beta-D-glucopyranosyl-4'-O-alpha-L-rhamnopyranosyl apigenin via a hexanoyl ester-based protection strategy.
abstract: The first total synthesis of 7-O-beta-D-glucopyranosyl-4'-O-alpha-L-rhamnopyranosyl apigenin 1, which exhibits good anti-hepatitis B virus and anti-stroke activities, was accomplished in six steps and 20% overall yield from apigenin. Another synthetic route, in which the target was obtained in seven steps, was also developed to prove the utility of a hexanoyl ester-based orthogonal protection strategy. The hexanoyl protection strategy provided all the flavonoid intermediates with good solubility and reactivity, enabled efficient selective protection and glycosylation, and provided a practical and effective synthetic strategy for flavonoids, starting from commercially available flavone.
authors.affiliation: Shanghai Institute of Pharmaceutical Industry, Shanghai, China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Gao
authors.forename: Gaoyan
authors.initials: G
authors.lastname: Lian
authors.forename: Feng
authors.initials: F
authors.lastname: Lin
mesh_terms: D047310:Apigenin / Q000138:chemical synthesis* / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D008956:Models, Chemical; D015394:Molecular Structure
chemical_list: D005419:Flavonoids; D006027:Glycosides; D047310:Apigenin