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Synfacts 2014; 10(2): 0113
DOI: 10.1055/s-0033-1340561
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Biogenetically Inspired Synthesis of Indole Alkaloids

Contributor(s):
Erick M. Carreira
,
Simon Krautwald
Mizoguchi H, Oikawa H, Oguri H * Hokkaido University, Sapporo and Japan Science and Technology Agency PRESTO, Kawaguchi, Japan
Biogenetically Inspired Synthesis and Skeletal Diversification of Indole Alkaloids.

Nature Chem. 2014;
6: 57-64
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Further Information

Publication History

Publication Date:
20 January 2014 (online)

 
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Key words

iboga alkaloids - aspidosperma alkaloids - andranginine alkaloids - indole alkaloids - biomimetic synthesis - [4+2] cyclization - dihydropyridines

Significance

Oguri and co-workers report elegant and concise syntheses of several types of ­indole alkaloids. Their biogenetically inspired strategy relies on the use of a dihydropyridine intermediate that enables access to five skeletally distinct scaffolds.


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Comment

The key and multipotent intermediate D was prepared from C by copper-catalyzed ­dihydropyridine formation. By judicious choice of conditions, D could be converted into three structurally distinct natural products in very few steps.


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