Biosynthesis of porphyrins and related macrocycles. Part 49.1 Exploration of synthetic routes to analogues of the spiro-intermediate for porphyrin biosynthesis

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


Abstract

The proposed intermediacy of the spiro-pyrrolenine 1 for the biosynthesis of uroporphyrinogen III has focussed attention on its synthesis. Several different approaches to close analogues of this compound are explored, including (a) the synthesis of a dilactone bridged dipyrrolic pyrrolenine, (b) deactivation of two of the pyrrole rings of the macrocycle by attaching 3-methoxycarbonyl groups and (c) approaches to spiro-macrocyclic compounds via dipyrroketones. The chemistry of the different types of synthetic intermediates is described.


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