Abstract
Although Lewis acid-catalyzed condensation of 9-H dipyrrinones with acetone dimethylketal is known to afford 10,10-dimethyl-bilirubin analogs, stannic chloride-catalyzed condensation with acetone followed a different course to give a novel linear tetrapyrrole containing a C(9)–C(10)–N(23) linkage that forms a pyrrolizine unit with one of the internal pyrroles. The structures ( 1 and 2) of this unexpected new type of tetrapyrrole, which might be viewed as an N-inverted and N-bridged extended bilirubin, were characterized by a combination of mass spectrometry, NMR spectroscopy, and X-ray crystallography.
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