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DOI: 10.1039/A804588G (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 3241-3244

Syntheses of novel piperidin-4-ylphosphinic acid, and piperidin-4-ylphosphonic acid analogues of the inhibitory neurotransmitter 4-aminobutyric acid (GABA)

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Jan Kehler, Bjarke Ebert, Otto Dahl and Povl Krogsgaard-Larsen

Abstract

Piperidin-4-ylphosphinic acid, methyl(piperidin-4-yl)phosphinic acid and piperidin-4-ylphosphonic acid analogues of the GABAA agonist piperidin-4-ylcarboxylic acid (isonipecotic acid) were synthesised. The acid groups were introduced using a sequential Pudovik addition followed by a Barton deoxygenation procedure and finally followed by acidic hydrolysis. The mild and efficient procedure gave the target amino acids in good yields.

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