2 H N.m.r. spectroscopy has been used to establish the labeling patterns in retrorsine (1) derived biosynthetically from (R)-[1-2H]-putrescine; in the former case retrorsine (11) is equally labelled with 2H at the 3β, 5α, 8α and 9-pro-S positions, while with the latter precursor only the 3α and the 5β positions in retrorsine (15) are labelled with 2H.
J. Rana and D. J. Robins, J. Chem. Soc., Chem. Commun., 1984, 517 DOI: 10.1039/C39840000517
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