Methyl 3,4-dihydrosecoxyloganin (2a), readily obtained from secologanin (1), has been converted with retention of chirality at C-2 and C-7 into a piperidone (5) which acts as a general synthetic precursor for Ipecac alkaloids exemplified by deoxytubulosine (8b), cephaeline (9b), and emetine (9c).
R. T. Brown, A. G. Lashford and S. B. Pratt, J. Chem. Soc., Chem. Commun., 1979, 367 DOI: 10.1039/C39790000367
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