Journal of the Chemical Society. Perkin transactions I p. 2633 - 2642 (1996)
Update date:2022-08-03
Topics:
Leeper, Finian J.
Rock, Martin
Appleton, Diana
Syntheses are described of several analogues of porphobilinogen intended as substrates and/or inhibitors of porphobilinogen deaminase (hydroxymethylbilane synthase). 2-Methylporphobilinogen 12 has been synthesised from α-methylpyrrole 6, whereas a phosphonate analogue 20 of porphobilinogen, 8,9-didehydroporphobilinogen 26 and 9-fluoroporphobilinogen 38 have all been made from the 1H-pyrrolo[2,3-c]pyridine 14. The best route to 38 avoids fluoroacrylate 28 because of loss of fluorine during reduction of the double bond.
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Doi:10.1021/acs.orglett.8b02954
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