lycopodine

Description

This alkaloid has, so far, been discovered in all Lycopodium species with the exception of L. saururus Lam. It was first obtained by B6deker who assigned to it the formula C32Hs203N2, altered to that given by Achmatowicz and Uzieblo and confirmed by Manske and Marion. It forms colourless prisms from Et20 and has [α]²⁰_D - 9.01 ° (Me2CO). It yields crystalline salts and derivatives: the perchlorate, m.p. 276°C; methochloride, m.p. 238-240°C, methiodide, m.p. 335- 7°C and a hydrazone, mop. 20B-2l0°C. According to Bodeker it also yields a crystalline hydrochloride and aurichloride.
Even under pressure at 200°C in the presence of Raney Ni, the base cannot be hydrogenated. On selenium dehydrogenation, a complex mixture of bases is formed from which 7 -methylquinoline and 5:7 -dimethylquinoline have been identified. 7 -methylquinoline is also stated to be formed when the base is heated with palladium as catalyst. A stereospecific total synthesis of the (±)-form has been described.

Definition

ChEBI: Lycopodine is a quinolizidine alkaloid. It derives from a hydride of a lycopodane.

References

Bodeker., Annalen., 208,363 (1881)
Achmatowicz, Uzieblo., Rocz. Chern., 18,89 (1938)
Manske, Marion., Can. 1. Res., 20B, 87 (1942)
Marion, Manske., ibid, 20B, 153 (1942)
Manske, Marion., 1. Arner. Chern. Soc., 69,2126 (1947)
Anet., Tetrahedron Lett., 20, 13 (1960)
Harrison et al., Can. 1. Chern., 39,2086 (1961)