lythranidine

Description

A minor alkaloid obtained from Lythrum anceps Mak., the base is a colourless oil which is non-crystallizable. It contains one methoxyl group, a phenolic and two non-phenolic hydroxyl groups and a piperidine ring. The O-acetate is identical with Lythranine (q.v.) and the O,O,O-triacetate has been obtained as colourless crystals, m.p. 180-217°C (dec.); [α]²⁵_D - 27°. Methylation with CH2N2 gives a mixture of the O-methyl ether which is amorphous and the O,N-dimethyl derivative, colourless crystals, m.p. 167 _9°C. Oxidation of the former with KMn04 yields 2: 2'-dimethoxydiphenyl-5: 5'-dicarboxylic acid. When subjected to double Hofmann degradations, each followed by hydrogenation, the alkaloid gives a nitrogen-free base, C27H3S03, m.p. 13 2.5-134°C.

References

Fu;ita et al., Tetrahedron Lett., 4595 (1967) Fujita, Fuji, Tanaka., ibid, 5905 (1968) Fujita et al., Chem. Pharm. Bull., 18,2216, 2393 (1970) Fujita, Fuji, Tanaka., J. Chem. Soc., C, 205 (1971) Fujita, Fuji., ibid, 1651 (1971)