First total chemical synthesis of natural acyl derivatives of some phenolglycosides of the family Salicaceae

The total synthesis of certain natural phenolglycosides of the family Salicaceae, namely: salireposide, populosides A, B, and C and not occurring in plants desoxysalireposide (2-(β-d-glucopyranosyloxy)-benzylbenzoate) and per-acetate of iso-salireposide (2-(β-d-glucopyranosyloxy)-5-benzoyloxy benzyl alcohol), starting from readily available phenols and glucose was accomplished. A simple method for the synthesis of phenolglycosides derivatives of 2-acyloxy salicyl and gentisyl alcohol was developed. The key step of these natural products’ synthesis is a selective removal of acetyl groups in the presence of other acyl groups.

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► Total synthesis of natural phenolglycosides from available substrates is reported.
► Synthetic phenolglycosides are proved to be identical to natural phenolglycosides.
► We report acid-catalyzed acetyl group cleavage without breaking the glycosidic bond.