Abstract

98
P. M. Petersen, C. J. Hawker, N. P. J. Stamford, F. J. Leeper and A. R. Battersby
"Biosynthesis of porphyrins and related macrocycles. Part 50. Synthesis of the N-formyl-dihydro analogue of the spiro-intermediate and its interaction with uroporphyrinogen III synthase"
J. Chem. Soc., Perkin Trans. 1, 1998, 1531-1539. Full Text

The proposed intermediacy of the spiro-system for the biosynthesis of uroporphyrinogen III has focused attention on its synthesis. In this paper the approach that is explored is to carry a dihydropyrrole through the entire synthesis with the intention of converting it into a 2H-pyrrole (pyrrolenine) in one of the final steps. The chemistry of the different types of synthetic intermediates is described and also it is demonstrated that the N-formyl dihydropyrrole is a strong inhibitor of cosynthetase. The conclusion is reached that of all the possible routes to the spiro-pyrrolenine, that via the protected dihydropyrrole shows the greatest promise.

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