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Synlett 1999; 1999(3): 291-294
DOI: 10.1055/s-1999-2594
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Novel Tocopherol Compounds XI. Synthesis, Bromination and Oxidation Reactions of 3-(5-Tocopheryl)propionic Acid

Thomas Rosenau* , Wolf D. Habicher, Antje Potthast, Paul Kosma
  • *Christian-Doppler-Laboratory, University of Agricultural Sciences - Vienna, Muthgasse 18, A-1190 Vienna, Austria; Fax +43 (1) 3 60 06 60 59; E-mail: trosenau@edv2.boku.ac.at
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Publication Date:
31 December 1999 (online)

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3-(5-Tocopheryl)propionic acid (γ-tocopherol-5-propionic acid, 13) has been synthesized by a multi-step sequence involving the hetero-Diels-Alder reaction between O-methyl-C,O-bis-(trimethylsilyl)ketene acetal (10) and the ortho-quinone methide of α-tocopherol (5) as the key step. The title compound is the first 5a-substituted tocopherol that shows an oxidation behavior largely similar to α-tocopherol.

α-tocopherol - 5a-substituted tocopherols - ortho-quinone methide - ketene acetal - hetero-Diels-Alder reaction

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