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Synfacts 2008(1): 0005-0005  
DOI: 10.1055/s-2007-991490
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of ()-Aspidospermidine

Contributor(s): Philip Kocienski
I. Coldham*, A. J. M. Burrell, L. E. White, H. Adams, N. Oram
The University of Sheffield and Eli Lilly & Co. Ltd, Windlesham, UK
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

Syntheses of the Aspidosperma alkaloids abound but few are as short and efficient (40% overall) as the synthesis depicted in which an intramolecular [3+2] cycloaddition of an azo­methine ylide D is used to construct a tricyclic ring system in E from a simple acyclic precursor B. For a related approach, see W. H. Pearson and co-workers J. Org. Chem. 2004, 69, 1919.