79205-16-6Relevant articles and documents
Pyoluteorin Derivatives. II. Synthetic Approaches to Pyrrole Ring Substituted Pyoluteorins (1)
Cue, Berkeley W.,Chamberlain, Nancy
, p. 667 - 670 (2007/10/02)
A method for the regiospecific synthesis of 3-substituted 2-aroylpyrroles is described.These pyrroles, which are structurally related to the naturally occuring antibiotic pyoluteorin, are prepared by a Friedel-Crafts aroylation of 4-substituted pyrrole-3-carboxylic acid esters with 2,6-dimethoxybenzoyl chloride.The carboalkoxy group is then removed by hydrolysis and decarboxylation to produce isomerically pure 3-substituted-2-(2',6'-dimethoxybenzoyl)pyrroles (5 and 13).Conversion of these pyrroles into pyoluteorin-like coumpounds led to some unexpected products which arise from facile cleavage of the dihydroxybenzoyl portion of the molecules during chlorination.