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Synfacts 2009(3): 0246-0246  
DOI: 10.1055/s-0028-1087692
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Nankakurines A and B

Contributor(s): Philip Kocienski, Zofia Komsta
B. L. Nilsson, L. E. Overman*, J. R. de Alaniz, J. M. Rohde
University of California, Irvine, USA
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Publikationsverlauf

Publikationsdatum:
19. Februar 2009 (online)

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Significance

The nankakurines A and B are alkaloids isolated from the club moss Lycopodium hamiltonii. Nankakurine A induces secretion of neurotropic factors in human astrocytoma cells. The synthesis highlights a multigram, stereoselective Diels-Alder reaction (B + C → D) as well as a regioselective dipolar cycloaddition (F → G). The authors established the relative and absolute configuration of the target molecules.