Synthesis of xanthohumol and xanthohumol-d3 from naringenin

Abstract

A six-step synthesis of xanthohumol (1a) and its d₃-derivative (1b) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an α,β-conjugated ketone system. Compound 1b was used as an internal standard in stable isotope dilution assays of 1a in two Polish beers.