Total synthesis of [<sup>13</sup>
C]<sub>2</sub>
-, [<sup>13</sup>
C]<sub>3</sub>
-, and [<sup>13</sup>
C]<sub>5</sub>
-isotopomers of xanthohumol, the principal prenylflavonoid from hops
作者:Duncan C. Ellinwood、Mohamed F. El-Mansy、Layhna S. Plagmann、Jan F. Stevens、Claudia S. Maier、Adrian F. Gombart、Paul R. Blakemore
DOI:10.1002/jlcr.3571
日期:2017.12
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.
黄腐酚 [(E)-6'-甲氧基-3'-(3-methylbuten-2-yl)-2',4',4"-trihydroxychalcone],主要来自啤酒花的异戊二烯化黄酮类化合物,具有复杂的生物活性特征,和该化合物的 13 C 标记同位素有可能用作分子探针和研究代谢和作用方式的分析标准。1,3-[13 C]2-黄腐酚是通过对 Khupse 和 Erhardt 的全合成进行 7 个步骤的调整和 5.7% 的间苯三酚总产率,通过包含级联 Claisen-Cope 重排以安装 3'-来自 5'-异戊二烯基芳基醚和 1-[13 C]-2',4'-双(苄氧基甲氧基)-6'-甲氧基-3'-(3-甲基丁烯-2-基)之间的羟醛缩合的异戊二烯基部分苯乙酮和 1'-[13 C]-4-(甲氧基甲氧基)苯甲醛。甲基酮中的 13 C 原子来源于 1-[ 13 C]-乙酰氯,而芳基醛中的 13 C 原子来源于 [ 13