vobasine

Description

A further alkaloid occurring in Voacanga africana, the base forms cubic crystals from MeOH and is strongly laevorotatory with [α]²³_D- 158.5° (c 1.0, CHCI3) or - 148.3° (c 1.0, MeOH). The ultraviolet spectrum has two absorption maxima at 239 and 315 mμ. The alkaloid forms a hydrochloride as prismatic plates from MeOH, m.p. 245-8°C (dec.); [α]²²_D - 120.1° (c 1.0, MeOH); the methiodide, m.p. 212-4°C (dec.); [α]²³_D - 117.2° (c 1.0, MeOH) and the 2:4-dinitrophenylhydrazone as deep red crystals, m.p. 172-5°C.

Definition

ChEBI: An indole alkaloid that is vobasan in which the bridgehead methyl group is substituted by a methoxycarbonyl group and an additional oxo substituent is present in the 3-position.

References

Renner., Experientia, 15, 185 (1959) Renner, Prins., ibid, 17,209 (1961) Renneretal., Helv. Chim. Acta, 46,2186 (1963) Cava et al., Tetrahedron Lett., 53 (1963) Budzikiewicz et al., Bull. Soc. Chim. Fr., 1899 (1963)