Studies in Alkaloid Chemistry: Part I. Minor Alkaloids of Lycopodium flabelliforme; Part II. Model Studies leading to a synthesis of cularine

Abstract

Part I. The results of an investigation of the minor alkaloids of Lycopodium flabelliforme using elution chromatography and countercurrent distribution are presented. Several alkaloids not previously reported to occur in this species were isolated and identified. A new alkaloid, hydroxy-de-N-methyl-α-obscurine, has been isolated and a structure proposed for it on the basis of physical evidence. A sufficient quantity of Lycopodium alkaloid L.5 which we have named flabellidine was isolated to permit the elucidation of its structure. Part II. A synthesis of 9-xanthenemethylamine and its rearrangement to the ring-expanded alcohol under the condition of the Demjanov reaction is described.