Hsu Che-Sheng, Chou Ho-Hsuan, Fang Jim-Min
Department of Chemistry, National Taiwan University, Taipei 106, Taiwan.
Org Biomol Chem. 2015 May 21;13(19):5510-9. doi: 10.1039/c5ob00411j.
Antroquinonol, which was first isolated from a mushroom, Antrodia cinnamomea, found in Taiwan, is an anticancer compound with a unique core structure of 4-hydroxy-2,3-dimethoxycyclohex-2-enone carrying methyl, farnesyl and hydroxyl substituents in the 4,5-cis-5,6-trans configuration. A short synthesis of (±)-antroquinonol is accomplished in seven steps from 2,3,4-trimethoxyphenol, which is oxidized in methanol to a highly electron-rich substrate of 2,3,4,4-tetramethoxycyclohexadienone and then a Michael reaction with dimethylcuprate is performed as the key step, followed by alkylation, reduction and epimerization to incorporate the required substituents at three contiguous stereocenters.
安曲喹诺醇最初是从台湾发现的樟芝中分离出来的，它是一种抗癌化合物，具有独特的核心结构，即4-羟基-2,3-二甲氧基环己-2-烯酮，其4,5-顺式-5,6-反式构型带有甲基、法尼基和羟基取代基。(±)-安曲喹诺醇的简短合成从2,3,4-三甲氧基苯酚开始，经过七个步骤完成，该苯酚在甲醇中被氧化为高富电子的底物2,3,4,4-四甲氧基环己二烯酮，然后进行与二甲基铜酸盐的迈克尔反应作为关键步骤，接着进行烷基化、还原和差向异构化，以在三个相邻的立体中心引入所需的取代基。
