Feeding experiments with (2R)- and (2S)-[2-2H]putrescine on Senecio isatideus plants have shown that hydroxylation at C-7 of retronecine proceeds with retention of configuration and formation of the 1,2-double bond involves removal of the pro-S hydrogen and retention of the pro-R hydrogen at C-2 of retronecine.
E. K. Kunec and D. J. Robins, J. Chem. Soc., Chem. Commun., 1985, 1450 DOI: 10.1039/C39850001450
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