1. Total synthesis of [ 13 C] 2 -, [ 13 C] 3 -, and [ 13 C] 5 -isotopomers of xanthohumol, the principal prenylflavonoid from hops.
- Author
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Ellinwood DC, El-Mansy MF, Plagmann LS, Stevens JF, Maier CS, Gombart AF, and Blakemore PR
- Subjects
- Carbon Isotopes chemistry, Chemistry Techniques, Synthetic methods, Flavonoids chemistry, Isomerism, Propiophenones chemistry, Flavonoids chemical synthesis, Humulus chemistry, Propiophenones chemical synthesis
- Abstract
Xanthohumol [(E)-6'-methoxy-3'-(3-methylbuten-2-yl)-2',4',4″-trihydroxychalcone], he principal prenylated flavonoid from hops, has a complex bioactivity profile, and
13 C-labeled isotopomers of this compound are of potential use as molecular probes and as analytical standards to study metabolism and mode of action. 1,3-[13 C]2 -Xanthohumol was prepared by an adaptation of the total synthesis of Khupse and Erhardt in 7 steps and 5.7% overall yield from phloroglucinol by a route incorporating a cascade Claisen-Cope rearrangement to install the 3'-prenyl moiety from a 5'-prenyl aryl ether and an aldol condensation between 1-[13 C]-2',4'-bis(benzyloxymethyloxy)-6'-methoxy-3'-(3-methylbuten-2-yl)acetophenone and 1'-[13 C]-4-(methoxymethyloxy)benzaldehyde. The13 C-atom in the methyl ketone was derived from 1-[13 C]-acetyl chloride while that in the aryl aldehyde was derived from [13 C]-iodomethane. Tri- and penta-13 C-labeled xanthohumols were similarly prepared by applying minor modifications to the route., (Copyright © 2017 John Wiley & Sons, Ltd.)- Published
- 2017
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