This alkaloid occurs in Garrya species and is a major constituent of G. veatchii. It
is laevorotatory with [α]27.5D - 69.01°. The crystalline hydrochloride has m.p.
2Sl-2°C (dec.); hydrobromide, m.p. 229-2300 C and the hydriodide, m.p.
222-3°C (dec.). The O-acetate has m.p. l52-3°C and yields a hydrochloride,
m.p. 258-9°C. The structure has been determined by chemical analysis and
from spectroscopic data.
Wiesneretal., Can. J. Chem., 30,608 (1952)
Wiesner et al., Ber., 86,800 (1953)
Wiesner, Edwards., Experientia, 11,255 (1955)
Vorbrueggen, Djerassi., J. Amer. Chem. Soc., 84, 2999 (1962)
Nagata et al., ibid, 86,929 (1964)
Synthesis:
Valenta, Wiesner, Wong., Tetrahedron Lett., 2437 (1964)
Fujita, Fujita, Katayama., Tetrahedron, 26, 1009 (1970)
Wiesner et al., Experientia, 26, 471 (1970)
