ISOPTEROPIDINE

Description

Yeoh and his colleagues have obtained this alkaloid, possibly a stereoisomer of mitraphylline (q.v.) from Uncaria pteropoda. It yields colourless needles when crystallized from MeOH and has [α]¹⁹_D - 111 ° (c 1.0, CHC13 ). The ultraviolet spectrum shows an absorption maximum at 246 m/J. and a shoulder at 280 m/J.. It contains an imino group and forms a crystalline hydrochloride, m.p. 181-3°C; [α]_D - 123.6° (c 0.6, EtOH); a hydriodide, m.p. 216-8°C; [α]_D - 64° (c 1.1, EtOH); a methiodide, m.p. 217-9°C after softening at 210°C; [α]_D - 149.5° (c 0.5, EtOH) and the picrate, m.p. 147-8°C; [α]_D - 35° (c 0.6, EtOH).

References

Yeoh, Chan, Morsingh, Tetrahedron Lett., 931 (1966) Chan, Morsingh, Yeoh., J. Chem. Soc., C, 2245 (1966) Stereochemistry: Shamma et al., J. Amer. Chem. Soc., 89, 1739,2799 (1967)