vobasine

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.

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.

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)