Collective syntheses of phenylethanoid glycosides by interrupted Pummerer reaction mediated glycosylations

AbstractThe collective total syntheses of nine natural phenylethanoid glycosides (PhEGs) together with proposed Incanoside B in a divergent mode were described. By using a core disaccharide as common intermediate, our developed interrupted Pummerer reaction mediated (IPRm) glycosylations adopting latent-active strategy enables the efficient, concise and divergent syntheses of these bioactive PhEGs. Among them, five natural PhEGs, Darendoside B (1), Cistanoside G (3), Decaffeoyl acteoside (4), Kankanoside F (5) and 4′′′-epi-Leonoside F (7) were the first time being synthesized. According to the synthesis of 4′′′-epi-Leonoside F (7), we also elucidated the real structure of carbohydrate component of the PhEG isolated from Rehmannia glutinosa which was misled as “Leonoside F”.