(7R)-6,7,7aβ,8-Tetrahydro-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinolin-12-ol 7-oxide

Description

The alkaloid originally isolated under this name by Aston proved to be a mixture of laureline and pukateine and the name was then given to a third alkaloid occurring in the bark of Laurelia Novae-Zelandae. The base crystallizes in colOUrless needles or hexagonal tablets and is laevorotatory with [α]_D - 222° (CHCl 3 ). The sulphate hexahydrate, m.p. 99-l00°C is almost completely insoluble in H20; the methiodide has m.p. 249-250°C and the O,G-dimethyl ether forms colourless prisms, m.p. l34°C, b.p. 200-2l0°C/l0 mm; [α]_D - 314° (CHC13). The probable structure, given above, has been deduced by comparison with other, similar alkaloids although the alternative structure 3 :4-dihydroxy- 6:7-methylenedioxyaporphine, is not completely excluded.

References

Aston.,J. Chem. Soc., 97, 1381 (1910)
Barger, Girardet., Helv. Chim. Acta., 14, 481 (1931)
Girardet., ibid, 14, 504 (1931)
Govindachari et al., Chem. Ber., 91, 36 (1958)