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
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Paul M. Petersen, Craig J. Hawker, N. Patrick J. Stamford, Finian J. Leeper and Alan R. Battersby
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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