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A practical synthesis of pyoluteorin
Author(s) -
Cue Berkeley W.,
Dirlam John P.,
Czuba Leonard J.,
Windisch Wendell W.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180136
Subject(s) - pyrrole , chemistry , chloride , yield (engineering) , methylene , combinatorial chemistry , organic chemistry , metallurgy , materials science
A convenient, large‐scale synthesis of the antibiotic pyoluteorin, 2,3‐dichloro‐5‐(2′,6′‐dihydroxybenzoyl)‐pyrrole ( 1 ), is described. A key step in the synthesis involved a Friedel‐Crafts aroylation of pyrrole with 2,6‐dimethoxybenzoyl chloride ( 3 ) in methylene chloride. The desired intermediate, 2‐(2′,6′‐dimethoxybenzoyl)pyrrole ( 4 ), was obtained as the major product, along with a product of beta substitution ( 6 ). Compound 4 was converted to pyoluteroin ( 1 ) in four steps in an overall yield of 51%.