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Über die Chemie des Vitamins E. 1. Mitteilung. Die Umkehrung der Konfiguration am Kohlenstoffatom 2 von natürlichem (2 R , 4′ R , 8′ R )‐α‐Tocopherol
Author(s) -
Schudel P.,
Mayer H.,
Metzger J.,
Rüegg R.,
Isler O.
Publication year - 1963
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19630460134
Subject(s) - chemistry , tocopherol , ferric , stereochemistry , chloride , medicinal chemistry , antioxidant , vitamin e , organic chemistry
(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 (2 R , 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).