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Synthesis 2006(18): 3043-3047
DOI: 10.1055/s-2006-950190
DOI: 10.1055/s-2006-950190
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Polycitrin A and 3,4-Bis(4-hydroxyphenyl)pyrrole Derivatives Related to Polycitone A
Further Information
Received
22 May 2006
Publication Date:
15 August 2006 (online)
Publication History
Publication Date:
15 August 2006 (online)
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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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