The structure of thalmine
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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.
KeywordsMethyl Iodide Methoxyl Group Potassium Permanganate Liquid Ammonia Monoethanolamine
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