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Issue 9, 1998
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Biosynthesis of porphyrins and related macrocycles. Part 50.1 Synthesis of the N-formyl-dihydro analogue of the spiro-intermediate and its interaction with uroporphyrinogen III synthase

Abstract

The proposed intermediacy of the spiro-system 1 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 37 is a strong inhibitor of cosynthetase. The conclusion is reached that of all the possible routes to the spiro-pyrrolenine 1, that via the protected dihydropyrrole 30 shows the greatest promise.

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Article type: Paper
DOI: 10.1039/A708135I
Citation: J. Chem. Soc., Perkin Trans. 1, 1998,0, 1531-1540
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    Biosynthesis of porphyrins and related macrocycles. Part 50.1 Synthesis of the N-formyl-dihydro analogue of the spiro-intermediate and its interaction with uroporphyrinogen III synthase

    P. M. Petersen, C. J. Hawker, N. Patrick J. Stamford, F. J. Leeper and A. R. Battersby, J. Chem. Soc., Perkin Trans. 1, 1998, 0, 1531
    DOI: 10.1039/A708135I

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