title: On a novel chromanone-naphthalenetrione rearrangement related to vitamin E.
abstract: 4-Oxo-alpha-tocopherol (7) was synthesized in an efficient three-step procedure starting from alpha-tocopheryl acetate (1b) and rearranged under physiological conditions into naphthalenetrione 4, a minor vitamin E metabolite. The rearrangement involves a [4 + 2]-cycloaddition as the key step. [reaction: see text]
authors.affiliation: Institute of Chemistry, University of Agricultural Sciences, Vienna, Austria. trosenau@edv2.boku.ac.at
authors.forename: Thomas
authors.initials: T
authors.lastname: Rosenau
authors.forename: Antje
authors.initials: A
authors.lastname: Potthast
authors.forename: Gerald
authors.initials: G
authors.lastname: Ebner
authors.forename: Andreas
authors.initials: A
authors.lastname: Hofinger
authors.forename: Paul
authors.initials: P
authors.lastname: Kosma
mesh_terms: D000975:Antioxidants / Q000737:chemistry; D002021:Buffers; D006863:Hydrogen-Ion Concentration; D009285:Naphthoquinones / Q000737:chemistry*; D012997:Solvents; D014810:Vitamin E / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D002021:Buffers; D009285:Naphthoquinones; D012997:Solvents; C454804:stimon II metabolite; D014810:Vitamin E