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The alkaloids o f Lycopodi~rrn alopecuroides L. have been examined and seven alkaloids isolated. These include the known alkaloids lycopodine, lycodoline, and clavolonine, and three previously unreported alkaloids, alopecurine, debcnzoylalopecuri~~e, and alopecuridine. Anhydrolycodoline, prcviously obtained as a degradation product o f lycodoline, was also isolated. The properties o f the new alkaloids are described.

Evidence is presented in support of the stereostructures 4 and 5 for cirnicine and cirnicidine, respectively. Alkaloids 4 and 5, as well as the lactonic bases aspidophytine (23) and haplophytine (I), are converted by alkaline hydrogen peroxide to the corresponding 10-0x0 derivatives.On prCsente des preuves qui justifient I'attribution des sttrtostructures 4 e t 5 i la cimicine et i . la cirnicidine, respectivement. Les alcaloi'des 4 et 5, de rnCme que les bases lactoniq~les aspidophytine (23) et haplophytine (I), sont transformts par I'action de ptroxyde d'hydrogene alcalin en dtrivts 0x0-10.[Traduit par l e journal]Can. J . Chem., 51, 3102 (1973) Haplophytotz citnicidimz (Apocy~aceae) has been shown to contain a number of alkaloids of the aspidospermine type. Among these are the novel binuclear indole base haplophytine (1) (1-5), the carbinolaniine-ether bases haplocine (2) and haplocidine (3) (6), and the carbinolamine-lactone bases cimicine (7) and cimicidine (1, 2, 7).' In this paper, evidence is presented in support of the stereostructures 4 and 5 for cimicine and cimicidine, respectively, and some additional chemistry of these alkaloids is discussed. Cimicine, [a], + L 13" (CHCI,), has the molecular formula CzzH2,N20,. Its p.m.r. spectrum shows a number of points of similarity to that of its companion alkaloid hap-