A novel total synthesis of kinsenoside and goodyeroside A relying on the efficient reaction of the chiral 2(5H)-furanones.
A new total synthesis of the bioactive compounds, kinsenoside and goodyeroside A, has been accomplished from readily available starting materials. The chiral 2(5H)-furanone and its enantiomer were employed as the key chiral intermediates to construct the chiral glycosides and with the appropriate stereochemistry. The spectral data of the target compounds and their acetylated derivatives and are identical with those of the natural and corresponding acetylated products.
Zhang
Xiang
X
Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, 100050, China.
Huang
Hai-Hong
HH
Chen
Qing-Hun
QH
D015107:4-Butyrolactone / Q000031:analogs & derivatives; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013057:Spectrum Analysis; D013237:Stereoisomerism
C422363:3-glucopyranosyloxybutanolide; D005663:Furans; D009005:Monosaccharides; C507480:goodyeroside A; D015107:4-Butyrolactone