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Synfacts 2014; 10(2): 0113
DOI: 10.1055/s-0033-1340561
DOI: 10.1055/s-0033-1340561
Synthesis of Natural Products and Potential Drugs
Biogenetically Inspired Synthesis of Indole Alkaloids
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
20. Januar 2014 (online)
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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