A new synthesis of porphobilinogen analogues, inhibitors of hydroxymethylbilane synthaseElectronic supplementary information (ESI) available: Dixon plot. See http://www.rsc.org/suppdata/ob/b2/b209613g/

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Vol 1991 (04) ◽  
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Manfred Regitz
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XU Qun-Feng ◽  
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Rodrigo Rico ◽  
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: 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.


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