Description
The leaves of Lamprolobium fruticosum yields this alkaloid as a colourless oil,
[α]20Do + 29° (EtOH) and furnishing a crystalline picrate, m.p. 153-4°C. Acid
hydrolysis of the alkaloid yields glutaric acid and (+ )-l-aminoethylquinolizidine.
The stereochemistry of the latter has been established by demonstrating the
identity of the N-acetyl derivative, m.p. l44-5°C; [α]20Do + 46° (EtOH) with that
prepared from epilupinine. The structure has been confirmed from the infrared,
NMR and mass spectra. The total synthesis of the optically inactive alkaloid and
its epimer has been carried out.
References
Hart, Johns, Lamberton., Chem. Commun., 302 (1968)
Hart, Johns, Lamberton., Austral. J. Chem., 21, 1619 (1968)
Synthesis:
Jeffcoat., Diss. Abstr. Int., 30B, 4973 (1970)
Yamada, Hatano, Matsui., Agr. Bioi. Chem., 34, 1536 (1970)
