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Synfacts 2008(12): 1242-1242  
DOI: 10.1055/s-0028-1083565
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Alstonerine

Contributor(s): Philip Kocienski, Indu Dager
K. A. Miller, C. S. Shanahan, S. F. Martin*
The University of Texas at Austin, USA
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

(-)-Alstonerine belongs to the ­macroline family of alkaloids and exhibits cytotoxic activity against two human lung cancer cell lines. The key step, a Pauson-Khand reaction, was used to form the azabicyclo[3.3.1]nonane skeleton in B. A detailed study of various 2-allyl-6-­alkynyl-substituted piperidines and piperazines towards the Pauson-Khand reaction is discussed in the paper.