LYCOPODIUM ALKALOIDS: V. THE BROMINATION OF LYCOPODINE AND THE STRUCTURE OF ALKALOID L.20

Abstract
Monobromination of lycopodine hydrobromide in chloroform yields 6α-bromolycopodine hydrobromide, which can be epimerized to 6β-bromolycopodine hydrobromide. Hydrolysis of 6α-bromolycopodine proceeds with overall retention of configuration to give 6 α-hydroxylycopodine, which is identical with the Lycopodium lucidulum alkaloid L.20. On the basis of some of the rotatory dispersion data presented it is suggested that positively charged nitrogen has a negative specific rotativity.