L1NDENIANINE

Description

A sparteine derivative, lindenianine has been isolated from the aerial portions of Lupinus lindenianus found in the Andean Mountains. It is slightly laevorotatory with a specific rotation of [α]_D - 11 ° (c 1.3, CHCL3). The free base is best purified by recrystallization from a mixture of CHCL3 and Et2O. It forms a picrate as yellow needles from Me2CO-Et2O with m.p. 160-2°C and a monoacetyl derivative as a colourless oil which does not form a crystalline picrate. Catalytic hydrogenation with activated Pt02 furnishes dihydrodeoxylindenianine, m.p. 172-4°C; [α]_D - 13° (c 1.0, CHCL3) which forms a dipicrate, m.p. 118-121°C. Oppenauer oxidation with potassium tert-butoxide in C6H6 with 9-fluorenone gives the diketo derivative as yellow crystals from Et20, m.p. 173-6°C; [α]_D - 116° (c 1.0, CHCL3).

References

Nakano, Spinelli, Mendez,J. Org. Chem., 39,3584 (1974)