Strychnine (1) was reduced by lithium aluminium hydride to a carbinolamine (2), which was so readily converted into the enamine, 10,11-didehydrostrychnidine (3), that it could not be isolated in pure form. In the presence of acid, the enamine readily dimerised.
G. A. Swan and J. D. Wilcock, J. Chem. Soc., Perkin Trans. 1, 1972, 1068 DOI: 10.1039/P19720001068
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