In contrast to previous assumptions, the precursor of the monoterpenoid ipecac alkaloids cephaeline (6) and emetine (5), which arise from the condensation of dopamine (1) and secologanin (2), is α-deacetylisoipecoside (3a) and not its β-epimer deacetylipecoside (4a); the latter is the precursor of ipecoside (4b) and alangiside (7a) both of which possess the β-configuration.
N. Nagakura, G. Höfle and M. H. Zenk, J. Chem. Soc., Chem. Commun., 1978, 896 DOI: 10.1039/C39780000896
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