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Synfacts 2011(3): 0237-0237  
DOI: 10.1055/s-0030-1259404
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Paullone

Contributor(s): Philip Kocienski
D. R. Stuart*, P. Alsabeh, M. Kuhn, K. Fagnou
University of Ottawa, Canada
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Publication History

Publication Date:
16 February 2011 (online)

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Significance

The paullones inhibit three disease-relevant kinases, GSK-3, CDK-1, and CDK-5 as well as mitochondrial malate dehydrogenase. Most of them possess remarkable in vitro antiproliferative activity. The key step in the synthesis depicted is the oxidative annulation of acetanilide (F) with the internal alkyne E catalyzed by a dicationic rhodium(III) complex to give the indole G. Molecular oxygen is the terminal oxidant.