1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione

Description

The leaves of Lamprolobium fruticosum yields this alkaloid as a colourless oil, [α]²⁰_Do + 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]²⁰_Do + 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.

Definition

ChEBI: Lamprolobine is a member of quinolizines.

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)