Abstract

97
C. J. Hawker, P. M. Petersen, F. J. Leeper and A. R. Battersby
"Biosynthesis of porphyrins and related macrocycles. Part 49. Exploration of synthetic routes to analogues of the spiro-intermediate for porphyrin biosynthesis"
J. Chem. Soc., Perkin Trans. 1, 1998, 1519-1530. Full Text

The proposed intermediacy of the spiro-pyrrolenine 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.

Previous abstract

Next abstract