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Synlett 1999; 1999(3): 291-294
DOI: 10.1055/s-1999-2594
DOI: 10.1055/s-1999-2594
letter
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Novel Tocopherol Compounds XI. Synthesis, Bromination and Oxidation Reactions of 3-(5-Tocopheryl)propionic Acid
Further Information
Publication History
Publication Date:
31 December 1999 (online)
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