Lycopodium Alkaloids: Viii. Lycopodine

MacLean, David B.; Harrison, W. A.

doi:10.1139/v59-255

Cited by 6 publications

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“…The abromide I1 had been converted t o the corresponding acid and thence to the ring-A lacta~n IV. The infrared spectrum of the latter indicated that ring A was six-membered or larger (3). The p-bromide I11 had been converted to the corresponding acid which, on reduction with sodiunl borohydride, readily formed a lactone (V).…”

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“…The methyl ester, IX, of P-cyanolycopodine carboxylic acid (3) was converted by hydrolysis and subsequent treatment with diazomethane t o the methyl ester of the corresponding anlino acid. When the ester was heated under reflux in xylene it yielded the lacta~n X , C1,jI-I2302N, which showed absorption in the infrared a t 1626 cm-l indicative of a six-membered or larger lactam.…”

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Lycopodium Alkaloids: X. The Structure of Lycopodine

Harrison¹,

Curcumelli-Rodostamo²,

Carson³

et al. 1961

Can. J. Chem.

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Thc reactions leading to the establishment of structure I for lycopodine are discussed. S t r u c t~~r e s are proposed for three cyclizatioll products derived from lycopodine.I n a short comlnunication (1) we proposed structure I for lycopodine. This structure has been confirmed by the worlt of Anet (2), who succeeded in interconverting several Lycopodiz~m alkaloids, among which was lycopodine. In this paper we wish to give a full account of our worlt on the elucidation of the structure of the alltaloid and t o discuss the structures of the tetracylic compounds obtained on elimination of hydrogen halide from lycopodine methiodide and a-and P-cyanobromolycopodine.

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