Description
This novel alkaloid has been isolated from Sternona sessilifolia and S. tuberosa
and was first given the formula C19H29O4N, subsequently altered to that given
above. It crystallizes in colourless needles from MeOH with 1 mole of solvent,
m.p. 65-88°C (dec.) and has [α]
D - 25.4° (Me2CO). It is a non-phenolic,
tertiary base and yields a hydrobromide, m.p. 120°C (dec.) and a perchlorate,
m.p. 242°C (dec.). The methiodide monohydrate has m.p. 236-8°C (dec.) and
the methochloride, dihydrate, m.p. 172°C. A methosulphate has also been
prepared, m.p. 253°C (dec.). The base is not hydrolyzed by acids but in the
presence of excess PtO2 it gives the dihydro derivative, m.p. 133°C, furnishing a
hydrochloride, m.p. 281 ° C. Oxidation with KMnO4 gives a C17 compound,
whereas oxidation with silver oxide forms a neutral substance, C22H29O4N, m.p.
178°C which still contains the lactone groups and gives a positive Ehrlich
pyrrole reaction.
References
Kondo, Suzuki, Satomi.,J. Pharrn. Soc., Japan, 54,96 (1934)
Kondo, Suzuki, Satomi., ibid, 59, 177 (1939)
Kondo, Suzuki, Satomi., ibid, 60, 149 (1940)
Kondo, Suzuki, Satomi., ibid, 61, 111 (1941)
Kaneko., Ann. Rep. ITSUU Lab. (Tokyo), 11,45 (1960)
Gotz, Bogri, Gray., Tetrahedron Lett., 707 (1961)
Edwards, Feniak, Handa., Can. J. Chern., 40,455,2416 (1962)
Crystal structure:
Harada et ai., Chern. Cornrnun., 460 (1967)
