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Synfacts 2007(3): 0243-0243  
DOI: 10.1055/s-2007-968194
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of dl-Histrionicotoxin

Contributor(s): Philip Kocienski, Stewart Eccles
M. S. Karatholuvhu, A. Sinclair, A. F. Newton, M.-L. Alcaraz, R. A. Stockman*, P. L. Fuchs*
University of East Anglia, Norwich and AstraZeneca, Loughborough, UK; Purdue University, West Lafayette, USA
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Publikationsdatum:
20. Februar 2007 (online)

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Significance

Histrionicotoxin, isolated from the skin of numerous protected frog species, shows high activity as a non-competitive inhibitor of the central neuronal nicotinic acetylcholine receptors. Stockman and Fuchs have disclosed a concise route to dl-histrionicotoxin that utilizes sequential nitrone 1,3-dipolar cycloaddition reactions to access key tricycle G. For a synthesis of enantiopure histrionicotoxin employing a nitrone 1,3-dipolar cycloaddtion reaction, see: E. C. Davison et al. J. Chem. Soc., Perkin Trans. 1 2002, 1494-1514.