title: A short synthesis of (±)-antroquinonol in an unusual scaffold of 4-hydroxy-2-cyclohexenone.
abstract: 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.
authors: Department of Chemistry, National Taiwan University, Taipei 106, Taiwan. jmfang@ntu.edu.tw.
authors: Che-Sheng
authors: CS
authors: Hsu
authors: Ho-Hsuan
authors: HH
authors: Chou
authors: Jim-Min
authors: JM
authors: Fang
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D000478:Alkylation; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002725:Chloroform / Q000737:chemistry; D003511:Cyclohexanols / Q000737:chemistry*; D003512:Cyclohexanones / Q000737:chemistry*; D006868:Hydrolysis; D008968:Molecular Conformation; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D014451:Ubiquinone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C529503:4-hydroxy-2-cyclohexenone; D000097:Acetonitriles; D003511:Cyclohexanols; D003512:Cyclohexanones; D014451:Ubiquinone; D002725:Chloroform; C545357:antroquinonol; C032159:acetonitrile