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- W3025851947 abstract "Laudanosoline-4':6-dimethyl ether has been postulated as the phenolic precursor in the biogenesis of morphine alkaloids and aporphine alkaloids of the glaucine and corytuberine type. A thirteen-step unambiguous synthesis of laudanosoline-4':6-dimethyl ether is described starting from isovanillin. Oxidation of laudanosoline-4':6-dimethyl ether with alkaline potassium ferricyanide has been attempted under varying conditions of pH, concentration, phenol-oxidant ratio, reaction time, order of addition of the oxidant and phenol etc. The results of these experiments are discussed in the light of the spectroscopic and paper chromatographic properties of the oxidation products. Several experiments have been carried out to resolve authentic mixtures of aporphines and laudanosine by paper chromatography and the knowledge gained in these experiments has been successfully employed in the resolution of products obtained by the oxidation of laudanosoline-4':6-dimethyl ether with alkaline ferricyanide. In a number of experiments the Rf values of certain components of the oxidation product point to the formation of aporphines. An attempted synthesis of laudanosoline-4':6-diisopropyl ether, from papaverine via laudanosoline-3':7-dimethyl ether, the reported demethylation product of laudanosine, is described. 3-Isopropyl morphinone has been prepared from morphine and converted back into it." @default.
- W3025851947 created "2020-05-21" @default.
- W3025851947 creator A5006726311 @default.
- W3025851947 date "1958-01-01" @default.
- W3025851947 modified "2023-09-26" @default.
- W3025851947 title "Studies in biogenetic aspects of phenol oxidation" @default.
- W3025851947 hasPublicationYear "1958" @default.
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