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.
Department of Chemistry
University of Cambridge