The efficient total synthesis of bis-glycosyl apigenin from naringenin: a greener way.
An efficient total synthesis of 7-O-beta-D-glucopyranosyl-4'-O-alpha-L-rhamnopyranosyl apigenin (1) was developed in only four steps from naringenin. Compared with our previously reported first total synthesis route (six steps and 19.6% overall yield), this new route contained two steps of highly regioselective glycosylation without any selective protection steps. 7,4'-di-O-beta-D-glucopyranosyl apigenin (2) was also prepared efficiently by this method. The method is environmentally friendly, economical, and provides a greener method for flavonoid synthesis starting from an inexpensive flavanone.
Chen
Jianli
J
Shanghai Institute of Pharmaceutical Industry, Shanghai 200437, China.
Huang
Wei
W
Lian
Gaoyan
G
Lin
Feng
F
D047310:Apigenin / Q000138:chemical synthesis* / Q000737:chemistry*; D044950:Flavanones / Q000737:chemistry*; D006031:Glycosylation; D055772:Green Chemistry Technology / Q000191:economics / Q000379:methods*; D013237:Stereoisomerism; D013379:Substrate Specificity
D044950:Flavanones; D047310:Apigenin; C005273:naringenin