Synthesis of Polycitrin A and 3,4-Bis(4-hydroxyphenyl)pyrrole Derivatives Related to Polycitone A

Abstract

The oxidative condensation of 3-arylpyruvic acids with arylethylamines to give 3,4-diarylpyrrole-2,5-dicarboxylic acids was used for an efficient synthesis of polycitrin A (4). Investigation of the bromine-mediated degradation of acid 2b to maleimide 3b suggested that 2,5-dibromopyrrole (5) and 5,5-dimethoxy-3-pyrroline-2-one (6) are intermediates in this process. The debromo analogue of polycitone A (10) was prepared in two steps from pyrrole dicarboxylic acid diester 7.

Key words

biomimetic synthesis - bromination - marine alkaloids - pyrroles - polycitrins - polycitones

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