Synthesis of furostanol glycosides: discovery of a potent α-glucosidase inhibitor

A convenient approach to the synthesis of furostanol glycosides has been developed with the features of both highly efficient incorporation of a 26-O-beta-D-glucopyranosyl unit and ready formation of hemiketal ring E. The total syntheses of seven furostanol saponins including funlioside B, lilioglycoside, protobioside I, protodioscin, pallidifloside I, coreajaponins A and parisaponin I are efficiently achieved using an easily available 16 beta-acetoxy-22-oxo-26-hydroxy-cholestanic derivative as a powerful building block. The alpha-glucosidase inhibitory activity of the synthesized saponins is also evaluated, which reveals that funlioside B is a highly potential lead for developing alpha-glucosidase inhibitors.