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Issue 9, 1970
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Phenol oxidation and biosynthesis. Part XXI. The biosynthesis of the Erythrina alkaloids

Abstract

The incorporation of (+)- and (–)-N-norprotosinomenine into erythraline and erythratine in Erythrina crista galli has been investigated and the specific utilisation of the (+)-isomer has been demonstrated. Double-labelling experiments have shown that in the same system 5,6,8,9-tetrahydro-2,12-dimethoxy-7H-dibenz[d,f] azonine-3,11-diol and erysodienone are also genuine precursors. The nature of the symmetrical intermediate shown to be involved in the conversion of (+)-N-norprotosinomenine into (5S)-erysodienone, is discussed. Later stages in the biosynthesis of erythraline have been investigated and shown to follow the lines previously postulated. The point of formation of the methylenedioxy-group is apparently not critical.

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Article type: Paper
DOI: 10.1039/J39700001213
Citation: J. Chem. Soc. C, 1970,0, 1213-1218
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    Phenol oxidation and biosynthesis. Part XXI. The biosynthesis of the Erythrina alkaloids

    D. H. R. Barton, R. B. Boar and D. A. Widdowson, J. Chem. Soc. C, 1970, 0, 1213
    DOI: 10.1039/J39700001213

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