RAUBASINE (DL-Ajrnalicine)

Description

A yohimbine type alkaloid, this base occurs in Rauwolfia serpentina and is optically inactive. The ultraviolet spectrum in EtOH has absorption maxima at 227, 280 and 292 mil with a shoulder at 246 mil. The alkaloid may be character_x0002_ized as the crystalline hydrochloride, m.p. 289°C. On acid hydrolysis, the base furnishes an acid, m.p. 252° C (dec.). A methyl group and a methoxycarbonyl group are present. One nitrogen is tertiary, the other being in the form of an indole moiety.

References

Klohs et al., J. Amer. Chem. Soc., 76, 1332 (1954)
van Tamelen, Placeway., ibid, 83,2594 (1961)
Shamma, Richey., ibid, 85,2507 (1963)
Finch et al., Tetrahedron, 22, 1327 (1966)
Biosynthesis:
Battersby et ai., Chem. Commun., 46, 346 (1966)
Loew, Goeggel, Arigoni., ibid, 347 (1966)
Battersby e tal., ibid, 810, 812, 888, 890 (1966)
Synthesis:
van Tamelen et al., J. Amer. Chem. Soc., 91,7359 (1969)