Summary
1. On the basis of the isolation of 2-methoxy-1-1′-diphenyloxide-4′,5-dicarboxylic acid (I) it has been established that thalmidine and thalmine are bis-benzylisoquinoline bases.
2. By the preparation of (+)-N-methylisococlaurine and (+)-O-methylarmepavine it has been shown that thalmidine is identical with O-methylthalicberine.
3. The nature of the degradation products isolated shows that thalmine has the LL configuration.
4. Since the diaminodialdehydes obtained by the ozonolysis of the des-bases of O-methylthalmine, O-methyloxyacanthine, and hernandezine are not identical, structure (VII) (taking the degradation products into account) is proposed for thalmine.
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References
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Khimiya Prirodnykh Soedinenii, Vol. 2, No. 2, pp. 107–114, 1966
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Telezhenetskaya, M.V., Ismailov, Z.F. & Yunusov, S.Y. The structure of thalmine. Chem Nat Compd 2, 83–88 (1966). https://doi.org/10.1007/BF00567541
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DOI: https://doi.org/10.1007/BF00567541