Journal of the Chemical Society

Published by Royal Society of Chemistry
Print ISSN: 0368-1769
Auroglaucin (II) and fuscin (VIII) both arise completely from "acetate," the polyketide and terpene pathways both being involved. The extent of incorporation of Me·14CO2H into the two portions of the molecule is different.
Nicotine oxide, dihydronicotyrine oxide, 1′-methylanabasine oxide, and the oxide of 1-methyl-2-phenylhexahydroazepine (VI; R1=Ph, R 2=H), on heating, rearrange to products in which the oxygen is contained in the ring. With the azepine oxide, an unsaturated hydroxylamine is also produced. The rearrangement of nicotine oxide takes place, to some extent at least, by an intramolecular concerted mechanism.
The first and second dissociation constants of adrenaline, noradrenaline, 3-amino-1-phenylethanol, and catechol have been determined in aqueous solution at 25° by means of a glass electrode. The further ionisation of adrenaline and of noradrenaline in aqueous solution is considered, and the interference that arises in quantitative work from the oxidation of these compounds to adrenochrome and melanin-like compounds is discussed.
The conversion of a quintuply labelled reticuline into thebaine in the opium poppy has proved that demethylation of reticuline does not precede its further transformation in the plant into the morphine skeleton. The partial synthesis of the postulated initial dienone cyclisation product of reticuline has been accomplished from thebaine. This dienone is identical with the natural alkaloid salutaridine isolated by Professor K. A. Barnes. Salutaridine has been reduced to two epimeric salutaridinols. By appropriate tritium labelling the incorporation of salutaridine and of the salutaridinols into thebaine and morphine has been studied. Salutaridine and one of the salutaridinols are transformed by the plant into morphine alkaloids in remarkably high yield and without scrambling of the labels. Several of the final stages of the biosynthesis of morphine alkaloids are thus clearly defined and in accord with carlier hypotheses. Part of this work has been reported in preliminary form.
The action of thiophosgene on anthranilic acid led to 1,2-dihydro-2-thiono- 3,1-benoxazin-4-one which was isomerised by heat to 3, 1-benzothiazine-2 (1H),4-dione. Derivatives of both compounds are described.
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