5,6,8,14-Tetradehydro-6-methoxy-17-methyl-2,3-[methylenebisoxy]morphinan-7β-ol

Description

A morphine type alkaloid, this base is a minor constituent of the seeds of Papaver nudicaule var. amurense. It forms clusters of colourless crystals from Me2CO and has [α] ²² _D - 52° (c 1.0, CHCI3). The salts are crystalline and include the hydriodide, m.p. 198°C (dec.); perchlorate, m.p. 188°C (dec.) and the picrate, m.p. 150°C (dec.). The structure given above has been determined on the basis of the infrared, NMR and mass spectra.

References

Boit, Flentje., Naturwiss., 47,180 (1960)
Flentje, Dopke, Jeffs., ibid, 52,259 (1965)
Dopke, Flentje, Jeffs., Tetrahedron, 24,4459 (1968)
Absolute configuration: Barton et ai., Chern. Ber., 100,2457 (1967)
Circular dichroism: Snatzke, Wollenberg.,!. Chern. Soc., C, 1581 (1966)