A six-step synthesis of xanthohumol (1a) and its d-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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9038150 | PMC |
| http://dx.doi.org/10.1039/d1ra05443k | DOI Listing |
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