title: Total synthesis of (+)-antroquinonol and (+)-antroquinonol D.
abstract: The first total synthesis of (+)-antroquinonol and (+)-antroquinonol D, two structurally unique quinonols with a sesquiterpene side chain, is described. The route features an iridium-catalyzed olefin isomerization-Claisen rearrangement reaction (ICR), lactonization, and Grubbs olefin metathesis. The requisite α,β-unsaturation was achieved via the selenylation/oxidation protocol and elimination of β-methoxy group to provide two natural products from a common intermediate.
authors: Department of Chemistry, National Dong Hwa University , Hualien 97401, Taiwan.
authors: Rohidas S
authors: RS
authors: Sulake
authors: Chinpiao
authors: C
authors: Chen
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D055491:Antrodia / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007495:Iridium / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014451:Ubiquinone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000475:Alkenes; D001688:Biological Products; D012717:Sesquiterpenes; D014451:Ubiquinone; D007495:Iridium; C545357:antroquinonol