220077-26-9Relevant academic research and scientific papers
Total synthesis of [13C]2-, [13C]3-, and [13C]5-isotopomers of xanthohumol, the principal prenylflavonoid from hops
Ellinwood, Duncan C.,El-Mansy, Mohamed F.,Plagmann, Layhna S.,Stevens, Jan F.,Maier, Claudia S.,Gombart, Adrian F.,Blakemore, Paul R.
, p. 639 - 648 (2017/11/27)
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 13C-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-[13C]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-[13C]-2′,4′-bis(benzyloxymethyloxy)-6′-methoxy-3′-(3-methylbuten-2-yl)acetophenone and 1′-[13C]-4-(methoxymethyloxy)benzaldehyde. The 13C-atom in the methyl ketone was derived from 1-[13C]-acetyl chloride while that in the aryl aldehyde was derived from [13C]-iodomethane. Tri- and penta-13C-labeled xanthohumols were similarly prepared by applying minor modifications to the route.
An asymmetric synthesis of L-[3-13C]phenylalanine and L-[3- 13C]tyrosine from [13C]carbon monoxide
Takatori, Kazuhiko,Nishihara, Mikiko,Nishiyama, Yukie,Kajiwara, Masahiro
, p. 15861 - 15869 (2007/10/03)
L-[3-13C]Phenylalanine and L-[3-13C]tyrosine were synthesized. [α- 13C]Benzyl bromides were prepared from [13C]carbon monoxide via the palladium-catalyzed carboalkoxylation of aryl halides. The asymmetric carbon corresponding to the 2-position in phenylalanine was introduced by the diastereoselective alkylation of Dellaria's oxazinone with [α-13C]benzyl bromides. Finally, ethanolysis, deprotection, hydrogenolysis and acid hydrolysis of the resulting alkylated oxazinones gave L-[3- 13C]phenylalanine and L-[3-13C]tyrosine in high optical purity.
