Synthesis of pelargonidin 3-O-6″-O-acetyl-β-d-glucopyranoside, an acylated anthocyanin, via the corresponding kaempferol glucoside

The first total synthesis of pelargonidin 3-O-6″-O-acetyl-β-d-glucopyranoside, an acylated anthocyanin of magenta-colored Verbena flowers, was successfully carried out. The key intermediate, protected kaemferol 3-O-glucoside, was constructed by the Baker-Venkataraman rearrangement from a glucosyloxyacetophenone followed by Zn-Hg reduction to the corresponding acylated anthocyanin.