Lycopodium alkaloids phlegmarine

Nyembo et al. [15] proposed in 1978 that the amino acid 34 and other compounds of general structure 35> known as phlegmarines, the stereochemistry of which is not specified, may be intermediates involved in the biosynthesis of Lycopodium alkaloids. 

Katakawa K, Kitajima M, Yamaguchi K, Takayama H (2006) Three new phlegmarine-type Lycopodium alkaloids, lycoposerramines-X, -Y and -Z, having a nitrone residue, from Lycopodium serratum. Heterocycles 69 223-229... 

Tanaka T, Kogure N, Kitajima M, Takayama H (2009) Asymmetric total syntheses of cyclic-nltrone-containing phlegmarine-type Lycopodium alkaloids, lycoposerramines-X and -Z. J Org Chem 74 8675-8680... 

The first lycopodium alkaloid was isolated from the club moss Lycopodium complanatum by Bodeker as early as 1881 [18] much later its structure was shown to be lycopodine [19]. Since the first comprehensive review on lycopodium alkaloids was published in 1968 [20], new structures have been isolated and the chemistry and biology of this class of compounds have been reviewed several times [6-9, 21], According to Ayer [6], the lycopodium alkaloids are generally considered to comprise of four major classes. Compounds 1-4 are representatives of each group lycopodine 1 (class 1), lycodine 2 (class IT), fawcettimine 3 (class III), and phlegmarine 4 (miscellaneous class IV). 

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