Description
A major constituent of Lupinus nuttallii, this alkaloid is dextrorotatory with
[α]
24
D + 25.3 ± 0.9° (c 2.0, EtOH). It has been characterized as the perchlorate,
m.p. l70-2°C. Prolonged treatment with NaBH4 yields (-)-4/3-hydroxysparteine,
yielding a perchlorate, m.p. 248-2500 C. Oppenauer oxidation of the alkaloid
gives 2:4-dioxosparteine. The structure has been established by treatment of the
base with P20 S to give (+)-2-oxo-3:4-didehydrosparteine which, on catalytic
hydrogenation is converted into deoxynuttalline, identified as (+ )-lupanine by
comparison with an authentic specimen.
References
Goldberg, Balthis., 1. Chern. Soc., D, 660 (1969)
