Description
This alkaloid occurs in Narcissus poeticus, Pancratium maritium and Rhodo_x0002_phiala bifida. It yields long, colourless prisms when recrystallized from MeOH
and is laevorotatory with [α]25D - 74° (c 0.02, MeOH). The ultraviolet spectrum
has two absorption maxima at 241 and 292 mil. It yields a crystalline perchlorate, m.p. 163-6°C and a picrate, m.p. 249-2S2°C. Two non-phenolic
hydroxyl groups and one methylenedioxy group are present in the molecule.
The 2-a-O-acetate is an amorphous solid which cannot be obtained crystalline
but the 3-{3-0-acetate forms colourless crystals from MeOH, m.p. 213-6°C. The
O,O-diacetate, also crystalline, has m.p. 163-S°C. The O-methyl derivatives
occur naturally, the 2-methyl compound is Montanine (q.v.) and the 2:3-dimethyl
ether is Manthine (q.v.). The structure is based primarily upon the mass spectrum
fragmentation pattern.
References
Sandberg, Michel., Lloydia, 26, 78 (1963)
Structure:
Wildman, Brown.,J. Amer. Chem. Soc., 90,6439 (1968)
