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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.
Newson, Harriet L; Wild, Duncan A; Yeung, Sing Yee; Skelton, Brian W; Flematti, Gavin R; Allan, Jane E; Piggott, Matthew J.
Afiliação
  • Newson HL; 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.
  • Wild DA; 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.
  • Yeung SY; 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.
  • Skelton BW; 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.
  • Flematti GR; 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.
  • Allan JE; 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.
  • Piggott MJ; 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.
J Org Chem ; 81(8): 3127-35, 2016 Apr 15.
Article em En | MEDLINE | ID: mdl-27002792
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.
Assuntos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Derivados de Benzeno / Produtos Biológicos / Antraquinonas / Dioxinas / Éteres / Benzodioxóis / Antrodia Idioma: En Ano de publicação: 2016 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Derivados de Benzeno / Produtos Biológicos / Antraquinonas / Dioxinas / Éteres / Benzodioxóis / Antrodia Idioma: En Ano de publicação: 2016 Tipo de documento: Article