Alkaloids of Lycopodiumlucidulum Michx. Structure and properties of alkaloid L.23

Abstract

The minor alkaloids present among the strong bases of Lycopodiumlucidulum have been reinvestigated. Manske and Marion's alkaloid L.23 has been shown to be epimeric with lycodoline at C-12 and the nitrogen. A correlation between the two alkaloids has been achieved. The presence of a σ-coupled p interaction in the ultraviolet spectrum of lycopodine, lycodoline, and related compounds is described. A Cotton effect due to this chromophore has been detected by means of circular dichroism. The optical rotatory dispersion and circular dichroic properties of lycopodine, 12-epilycopodine, lycodoline, and alkaloid L.23 are discussed in terms of the absolute configuration assigned to these alkaloids.