Owing to their special stability and prominent biological activity, C-glycosylflavones and their chemical synthesis have recently attracted considerable attention in the field of glycoscience. A total synthesis of glycosylflavone parkinsonin B with specific stereoselectivity is reported herein. 2-Hydroxy-4,6-bis- methoxy acetophenone (3) was synthesized by one step in high regioselectivity under the optimal condition. The compound 3 was then glycosylated with O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) trichloroacetimidate (7) as active glycosyl donor with specific stereoselectivity to produce compound 8. Park-insonin B (1) was synthesized by the chalcone route from compound 8. The structures of target compound 1 and intermediates were confirmed by IR, MS, ¹H NMR spectra and element analysis.

Key words: O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) trichloroacetimidate, synthesis, glycosyla-tion, C-glycosylflavone, 2-hydroxy-4,6-bis-methoxyacetophenone