Pyrroles and related compounds. Part 38. Porphobilinogen synthesis

Abstract

A new synthesis of porphobilinogen (1) and its [6-¹³C]- and [6-¹⁴C]-derivatives, via porphobilinogen lactam, is reported. For the most part the synthesis follows established methods in pyrrole chemistry, but there are two significant advances which make the route attractive: (1) transformation of readily available acetylpyrroles into methoxycarbonylmethylpyrroles by using thallium(III) nitrate in methanol, and (2) introduction of the aminomethyl function into porphobilinogen by cleavage of a phthalimidomethyl substituent.