Some new Lycopodium alkaloids

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Abstract
The alkaloids of the club moss Lycopodiumobscurum L., collected in Northern Alberta, have been investigated. The known alkaloids lycopodine, lycodine, clavolonine, dihydrolycopodine, O-acetyldehydrolycopodine, flabelliformine, β-lofoline, lycofoline, and des-N-methyl-α-obscurine were isolated and identified, as were the known compounds des-N-methyl-β-obscurine and acrifolinol. α-Obscurine and β-obscurine were not detected. The structures of the previously unreported alkaloids hydroxypropyllycodine (9a), lyconnotinol (11a), lobscurinol (19a), epilobscurinol (19b), and acetyllobscurinol (19c) are presented. Hydroxypropyllycodine (9a) is the first 19-carbon Lycopodium alkaloid reported to date. Its possible biogenetic significance is discussed. The isolation of obscurinine (14) and isoobscurinine (15) are reported and the preparation of obscurinine (15) by treatment of lobscurine (18) with ammonia is described. It is suggested that obscurinine and isoobscurinine are artefacts produced during the isolation process. Keywords: alkaloids, Lycopodium alkaloids, obscurinine, Lycopodiumobscurum, biogenesis.

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