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• W2764244369 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. The 13 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." @default.
• W2764244369 created "2017-10-20" @default.
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• W2764244369 date "2017-11-20" @default.
• W2764244369 modified "2023-09-27" @default.
• W2764244369 title "Total synthesis of [¹³ C]₂ -, [¹³ C]₃ -, and [¹³ C]₅ -isotopomers of xanthohumol, the principal prenylflavonoid from hops" @default.
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• W2764244369 doi "https://doi.org/10.1002/jlcr.3571" @default.
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