2β-(1-Hydroxy-1-methylethyl)-4-methoxy-2,3-dihydrofuro[2,3-b]quinoline

Description

This furoquinoline alkaloid was first isolated from Platydesma campanulata Mann and subsequently found in Geijera salicifolia Schott. It crystallizes from C6H6-light petroleum in white needles and has [α]²⁵_D + 43° (CHCl3). The ultraviolet spectrum in EtOH contains several absorption maxima at 229.3, 238.1, 253.5,262.3,272,283,307.2 and 320.5 mJ.l. with a shoulder at 294.5 mil. The methiodide forms colourless plates from EtOH, m.p. 1 62-4°C and the picrate has m.p. 107-9°C after softening at 93°C. The optically inactive base, obtained as prisms from a mixture of MeOH and isopropyl ether, melts at 137 -SoC and gives a picrate melting over a very wide temperature range from 96-l22°C.

Definition

ChEBI: Platydesmine is an organonitrogen heterocyclic compound, an oxacycle and an organic heterotricyclic compound.

References

Werner, Schuer., Tetrahedron, 19, 1293 (1963)
Bowman, Grundon., Chem. Commun., 334 (1965)
Bowman, Grundon.,J. Chem. Soc., C, 1504 (1966)
Johns, Lamberton., Austral. J. Chem., 19,1991 (1966)
Boyd, Grunson., Tetrahedron Lett., 2637 (1967)