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Lycojaponicumins A-C, three alkaloids with an unprecedented skeleton from Lycopodium japonicum.
Xiao-Jing Wang
1 ,
Gui-Jie Zhang ,
Peng-Yu Zhuang ,
Yan Zhang ,
Shi-Shan Yu ,
Xiu-Qi Bao ,
Dan Zhang ,
Yu-He Yuan ,
Nai-Hong Chen ,
Shuang-gang Ma ,
Jing Qu ,
Yong Li
May 18 2012
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Abstract
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.