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-beta-D-glucopyranoside, an acylated anthocyanin of magenta-col-ored Verbena flowers, was successfully carried out. The key intermediate, protected kaemferol 3-O-glucoside, was constructed by the Baker-Venkataraman rearrangement from a glycosyloxyacetophenone followed by Zn-Hg reduction to the corresponding acylated anthocyanin. (C) 2007 Elsevier Ltd. All rights reserved.