Description
Both Heirnia rnyritifolia Cham. et Schl. and H. salicifolia Link & Otto yield this
macrocyc1ic alkaloid which may be crystallized from a mixture of AcOEt, MeOH
and light petroleum as glistening needles. Two somewhat different values for the
specific rotation have been recorded, viz. [α]25D - 174.2° (c 0.3325, CHC13) by
Blomster and [α]25D - 153.4° (c 0.3, CHCI3) by Douglas. The ultraviolet spectrum exhibits a broad absorption maximum at 292 mil and an inflexion at
250 mil. Two methoxyl groups, a secondary and a phenolic hydroxyl group are
present. The hydrochloride yields colourless crystals from MeOH, m.p. 330°C
(dec.). The structure has been determined mainly from the infrared and mass
spectra.
References
Douglas et ai., L/oydia, 27, 25 (1964)
Blomster, Schwarting, Bobbitt., ibid, 27, 15 (1964)
Absolute configuration:
Chu et ai., Chern. Ind., 1795 (1966)
Mass spectrum:
Appel, Achenbach., Tetrahedron Lett., 5789 (1966)
Structure:
Ferris, Boyce, Briner., J. Arner. Chern. Soc., 93, 2942 (1971)
Ferris et ai., ibid, 93, 2963 (1971)
