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A Short Synthesis of the Plant Alkaloid 4-Methyl-2,6-naphthyridine

Author(s):

Alexandra Kamlah and Franz Bracher*   Pages 1 - 4 ( 4 )

Abstract:


A new synthesis of the 2,6-naphthyridine alkaloid 4-methyl-2,6-naphthyridine from Antirrhinum 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.

Keywords:

alkaloid, naphthyridine, oxidation, annulation, Suzuki-Miyaura coupling, enol ether

Affiliation:

Department of Pharmacy – Center for Drug Research, Ludwig-Maximilians University, Butenandtstr. 5-13, 81377 Munich, Department of Pharmacy – Center for Drug Research, Ludwig-Maximilians University, Butenandtstr. 5-13, 81377 Munich



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