Studies in Biogenetic Aspects of Phenol Oxidation

Jain, Megh K (1958) Studies in Biogenetic Aspects of Phenol Oxidation. PhD thesis, University of Glasgow.

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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.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry
Date of Award: 1958
Depositing User: Enlighten Team
Unique ID: glathesis:1958-79283
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 05 Mar 2020 11:06
Last Modified: 05 Mar 2020 11:06

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