On a novel chromanone-naphthalenetrione rearrangement related to vitamin E.
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]
Rosenau
Thomas
T
Institute of Chemistry, University of Agricultural Sciences, Vienna, Austria. trosenau@edv2.boku.ac.at
Potthast
Antje
A
Ebner
Gerald
G
Hofinger
Andreas
A
Kosma
Paul
P
D000975:Antioxidants / Q000737:chemistry; D002021:Buffers; D006863:Hydrogen-Ion Concentration; D009285:Naphthoquinones / Q000737:chemistry*; D012997:Solvents; D014810:Vitamin E / Q000737:chemistry*
D000975:Antioxidants; D002021:Buffers; D009285:Naphthoquinones; D012997:Solvents; C454804:stimon II metabolite; D014810:Vitamin E