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Synfacts 2009(4): 0360-0360  
DOI: 10.1055/s-0028-1088081
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Allosecurinine

Contributor(s): Philip Kocienski, Arndt W. Schmidt
A. B. Leduc, M. A. Kerr*
The University of Western Ontario, London, Canada
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Publication History

Publication Date:
23 March 2009 (online)

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Significance

Securinega alkaloids, which are isolated from Euphorbiaceae plants, display antimalarial, antifungal, antibiotic and GABA receptor antagonist activities. This synthesis of allosecuri­nine features a diastereoselective Yβ-catalyzed perhydropyrroloisoxazolidine formation followed by reductive N-O bond cleavage to give 2,5-cis-pyrrolidines.