A practical synthesis of pyoluteorin
| Autor: | Wendell W. Windisch, Berkeley W. Cue, John P. Dirlam, Leonard J. Czuba |
|---|---|
| Rok vydání: | 1981 |
| Předmět: | |
| Zdroj: | Journal of Heterocyclic Chemistry. 18:191-192 |
| ISSN: | 1943-5193 0022-152X |
| DOI: | 10.1002/jhet.5570180136 |
| Popis: | 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%. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text