Lycojaponicumins A–C, Three Alkaloids with an Unprecedented Skeleton from Lycopodium japonicum

Lycojaponicumins A–C (1–3), three trace alkaloids isolated from Lycopodium japonicum, represent a unique heterocyclic skeleton formed by the new linkage C4–C9. Notably, lycojaponicumins A and B (1 and 2) are the first examples of natural products possessing a 5/5/5/5/6 pentacyclic ring system with a...

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Bibliographic Details
Published in:Organic letters 2012-05, Vol.14 (10), p.2614-2617
Main Authors: Wang, Xiao-Jing, Zhang, Gui-Jie, Zhuang, Peng-Yu, Zhang, Yan, Yu, Shi-Shan, Bao, Xiu-Qi, Zhang, Dan, Yuan, Yu-He, Chen, Nai-Hong, Ma, Shuang-gang, Qu, Jing, Li, Yong
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Azabicyclo Compounds - chemistry
Azabicyclo Compounds - isolation & purification
Crystallography, X-Ray
Lycopodium - chemistry
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
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Summary:Lycojaponicumins A–C (1–3), three trace alkaloids isolated from Lycopodium japonicum, represent a unique heterocyclic skeleton formed by the new linkage C4–C9. Notably, lycojaponicumins A and B (1 and 2) are the first examples of natural products possessing a 5/5/5/5/6 pentacyclic ring system with a 1-aza-7-oxabicyclo[2.2.1]heptane moiety. These structures were elucidated by spectroscopic methods and X-ray diffraction analysis. A plausible biogenetic pathway was proposed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3009478