- A short synthesis of (±)-actinidine
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The monoterpene alkaloid (±)-actinidine 10 is prepared in 5 steps from 3,4-dimethylpyridine using a pyridine radical cyclisation for the formation of the cyclopentano[c]pyridine skeleton.
- Jones, Keith,Escudero-Hernandez, Maria L.
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- A short synthesis of the plant alkaloid 4-methyl-2,6-naphthyridine
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A new synthesis of the 2,6-naphthyridine alkaloid 4-methyl-2,6-naphthyridine from Antir-rhinum majus has been developed. Key steps are a regioselective oxidation of 3-bromo-4,5-dimethylpyridine to the corresponding 4-formyl derivative, and the annulation of the second pyridine ring by Suzuki-Miyaura cross-coupling using (E)-2-ethoxyvinylboronic acid pinacol ester as a masked acetaldehyde equivalent. This protocol gives the alkaloid in four steps starting from commercially available 3,4-dimethylpyridine in 15% overall yield. This annulation protocol should be useful for the synthesis of other condensed pyridines as well.
- Kamlah, Alexandra,Bracher, Franz
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p. 931 - 934
(2019/11/22)
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