Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
(2 S, 4′R, 8′R)-α-Tocopherol with unnatural configuration at C-2 is prepared by oxidation of natural, so called d-α-tocopherol (I), which has the (2R, 4′R, 8′R)-configuration, to α-tocopherylquinone (II), followed by recyclization of the corresponding α-tocopherylhydroquinone (III). Experiments showed that the configuration of carbon atom 2 of natural α-tocopherol is retained during the ferric chloride oxidation (I →II) and is predominantly inverted by zinc chloride cyclization of α-tocopherylhydroquinone (III).
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