4.8 Article

Isopalhinine A, a Unique Pentacyclic Lycopodium Alkaloid from Palhinhaea cernua

Journal

ORGANIC LETTERS
Volume 15, Issue 14, Pages 3570-3573

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol401411m

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Funding

  1. National Natural Science Foundation [U0932602, 90813004]
  2. National Basic Research Program (973 Program) of China [2011CB915503, 2009CB522303]

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A new pentacyclic (5/6/6/6/7) Lycopodium alkaloid named isopalhinine A (1), which possesses a sterically congested architecture built with a tricyclo[4.3.1.0(3,7)]decane (isotwistane) moiety and a 1-azabicyclo[4.3.1]decane moiety, and palhinines B (2) and C (3) were isolated from Palhinhaea cernua. The structure and absolute configuration of 1 were elucidated by a combination of NMR spectra, optical rotation calculation, and X-ray diffraction experiment. A possible biogenetic pathway was also proposed.

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