Lyconadins C and F, new Lycopodium alkaloids from Lycopodium complanatum

Kan'ichiro Ishiuchi, Takaaki Kubota, Haruaki Ishiyama, Shigeki Hayashi, Toshiro Shibata, Jun'ichi Kobayashi

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

New Lycopodium alkaloids, lyconadins C (1) and F (2), were isolated from the club moss Lycopodium complanatum. Lyconadin C (1) is a new C 16N2-type Lycopodium alkaloid possessing unique fused-tetracyclic ring system consisting of a cycloheptene ring fused to a decahydroquinoline and pyridone rings. Lyconadin F (2) possesses a primary amide moiety in its molecular, which is the first example of Lycopodium alkaloids. Biogenetically, lyconadins C (1) and F (2) might be related to lyconadins A (4) and B (5). The structures and relative stereochemistry of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute stereochemistry of 2 was elucidated by chemical correlations with lyconadin B (5) through hemiaminal form of lyconadin F (3).

Original languageEnglish
Pages (from-to)289-292
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number2
DOIs
Publication statusPublished - Jan 12 2011
Externally publishedYes

Keywords

  • Lyconadin C
  • Lyconadin F
  • Lycopodium alkaloids
  • Lycopodium complanatum

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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