The Alkaloids of Lycopodium Annotinum L.: A Study of Diphenylannotinine and Two of the Minor Alkaloids

Abstract

Part (i) -The Minor Alkaloids: Annotoxine, C32H44O5N2, has now been isolated from a Canadian source. It has been separated into the alkaloids acrifoline, C16H23O2N, and annotine (alkaloid L 11), C16H21O3N. Both alkaloids have been shown to possess one hydroxyl group, one carbonyl group and one centre of unsaturation. The lack of reactivity of the third oxygen function of annotine suggests that it is present in an ether linkage. The identity of O-acetylacrifoline with alkaloid L 12 has also been proved. Part (ii) -Diphenylannotinine: Diphenylannotinine has been shown to be C28H33O3N. It possesses two hydroxyl groups, the third oxygen is present in an ether linkage. The exact nature of the ether linkage could not be ascertained on the basis of the experimental evidence.