The first total synthesis of 7-O-beta-D-glucopyranosyl-4'-O-alpha-L-rhamnopyranosyl apigenin via a hexanoyl ester-based protection strategy.
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.
Gao
Qi
Q
Shanghai Institute of Pharmaceutical Industry, Shanghai, China.
Lian
Gaoyan
G
Lin
Feng
F
D047310:Apigenin / Q000138:chemical synthesis* / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D008956:Models, Chemical; D015394:Molecular Structure
D005419:Flavonoids; D006027:Glycosides; D047310:Apigenin