Fawcettimine alkaloids lycoposerramine

Katakawa K, Kogure N, Kitajima M, Takayama H (2009) A new Lycopodium alkaloid, lycoposerramine-R, with a novel skeleton and three new fawcettimine-related alkaloids from Lycopodium serratum. Helv Chim Acta 92 445-452 and references cited therein... 

Nakayama A, Kitajima M, Kogure N, Takayama H (2009) First asymmetric total syntheses of fawcettimine-type Lycopodium alkaloids, lycoposerramine-C and phlegmariurine-A. Org Lett 11 5554-5557... 

A series of lycoposerramines isolated by Takayama et al. were fawcettimane-type and fawcettidane-type alkaloids from the same species Lycopodium serratum in Japan which contains huperzines in China. The structure of lycoposerramine-A (21), which has a l,2,4-oxadiazolidin-5-one residue in the molecule, was elucidated through spectroscopic data and X-ray analysis (31,32). Seven new alkaloids, lycoposerramines B (22), C (23), D (24), E (25), P (26), Q (27), S (28), and U (29), with novel, fawcettimine-related structures were isolated from the club moss Lycopodium serratum in Japan (33). Their relative and absolute stereochemistries were analyzed by spectroscopic data. X-ray analysis, and chemical correlations. The skeleton of lycoposerramine A (21) may be constructed by the incorporation of NH3, NH2OH, and a Ci unit into a fawcettimine-type skeleton. 

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