4,7-Dihydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one

Description

The fresh bulbs of many species of Narcissus yield this alkaloid, together with the preceding base. It resembles narciclasine in that although the structure is clearly related to those of the Amaryllidaceous alkaloids it shows no basic properties since the nitrogen is amidic in character. The ultraviolet spectrum in EtOH is quite complex having absorption maxima at 233, 257, 274, 295, 322, 337 and 353 mil. It contains a methylenedioxy group and two phenolic hydroxyl groups and furnishes the diacetate which crystallizes from MeOH with m.p. 247°C. The corresponding dimethyl ether is amorphous with melting point above 320°C.

References

Piozzi et al., Tetrahedron, 24, 1119 (1968)
Revised structure: Mondon, Krohn., Tetrahedron Lett., 2123 (1970)
Mondon, Krohn., Chem. Ber., 103,2729 (1970)
Savona, Piozzi, Marino., Chem. Commun., 1006 (1970)