Abstract

82
F. J. Leeper, M. Rock and D. Appleton
"Synthesis of Analogues of Porphobilinogen"
J. Chem. Soc., Perkin Trans. 1,1996, 2633-2642. Full Text

Syntheses are described of several analogues of porphobilinogen intended as substrates and/or inhibitors of porphobilinogen deaminase (hydroxymethylbilane synthase). 2-Methylporphobilinogen was synthesised from 2-methylpyrrole, whereas a phosphonate analogue of porphobilinogen, 8,9-dehydroporphobilinogen and 9-fluoroporphobilinogen were all made from the azaindole. The best route to avoided fluoroacrylate because of loss of fluorine during reduction of the double bond.

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