title: Access to 1,2,3,4-Tetraoxygenated Benzenes via a Double Baeyer-Villiger Reaction of Quinizarin Dimethyl Ether: Application to the Synthesis of Bioactive Natural Products from Antrodia camphorata.
abstract: The first systematic investigation into the Baeyer-Villiger reaction of an anthraquinone is presented. The double Baeyer-Villiger reaction of quinizarin dimethyl ether is viable, directly providing the dibenzo[b,f][1,4]-dioxocin-6,11-dione ring-system, which is otherwise difficult to prepare. This methodology provides rapid access to 1,2,3,4-tetraoxygenated benzenes, and has been exploited by application to the total synthesis of a natural occurring benzodioxole and its biphenyl dimer, which both display noteworthy biological activity. Interestingly, the axially chiral biphenyl was found to be configurationally stable, but the resolved enantiomers exhibit no optical activity at the αD-line.
authors.affiliation: School of Chemistry and Biochemistry, ‡Centre for Microscopy, Characterisation and Analysis, §School of Medicine and Pharmacology, The University of Western Australia , Perth, WA 6009, Australia.
authors.forename: Harriet L
authors.initials: HL
authors.lastname: Newson
authors.affiliation: School of Chemistry and Biochemistry, ‡Centre for Microscopy, Characterisation and Analysis, §School of Medicine and Pharmacology, The University of Western Australia , Perth, WA 6009, Australia.
authors.forename: Duncan A
authors.initials: DA
authors.lastname: Wild
authors.affiliation: School of Chemistry and Biochemistry, ‡Centre for Microscopy, Characterisation and Analysis, §School of Medicine and Pharmacology, The University of Western Australia , Perth, WA 6009, Australia.
authors.forename: Sing Yee
authors.initials: SY
authors.lastname: Yeung
authors.affiliation: School of Chemistry and Biochemistry, ‡Centre for Microscopy, Characterisation and Analysis, §School of Medicine and Pharmacology, The University of Western Australia , Perth, WA 6009, Australia.
authors.forename: Brian W
authors.initials: BW
authors.lastname: Skelton
authors.affiliation: School of Chemistry and Biochemistry, ‡Centre for Microscopy, Characterisation and Analysis, §School of Medicine and Pharmacology, The University of Western Australia , Perth, WA 6009, Australia.
authors.forename: Gavin R
authors.initials: GR
authors.lastname: Flematti
authors.affiliation: School of Chemistry and Biochemistry, ‡Centre for Microscopy, Characterisation and Analysis, §School of Medicine and Pharmacology, The University of Western Australia , Perth, WA 6009, Australia.
authors.forename: Jane E
authors.initials: JE
authors.lastname: Allan
authors.affiliation: School of Chemistry and Biochemistry, ‡Centre for Microscopy, Characterisation and Analysis, §School of Medicine and Pharmacology, The University of Western Australia , Perth, WA 6009, Australia.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Piggott
mesh_terms: D000880:Anthraquinones / Q000737:chemistry*; D055491:Antrodia / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D052117:Benzodioxoles / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D004147:Dioxins / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000880:Anthraquinones; D001555:Benzene Derivatives; D052117:Benzodioxoles; D001688:Biological Products; D004147:Dioxins; D004987:Ethers; C000610680:quinizarin dimethyl ether