Pseudomonas bromoutilis

A synthesis of the marine antibiotic from Pseudomonas bromoutilis has been achieved by 1,3-dipolar cycloaddition of the oxazolone (388) with diethyl acetylenedicarboxylate (73CI(L)275). Hydrolysis and decarboxylation gave the pyrrole (390), identical with a sample prepared previously by other workers, and converted by them to pentabromopseudilin (391 Scheme 85) (66JA4509). 

Several species of marine bacteria are also known to produce bromine-containing compounds. Pseudomonas bromoutilis (Burkholder et al., 1960) and an undescribed Chromobacterium sp. (Anderson et al., 1974) have been shown to produce, among other compounds, the pyrrole derivative 3, which contains 72% bromine by weight. The list of halogenating microorganisms will no doubt grow as more is learned about these organisms. The major... 

This procedure was applied to the syntheses of pentabromo- and pentachloro-pseudilin. Pentabromopseudilin (20) was isolated from Pseudomonas bromoutilis [32, 33] and amarine species of Chromobacterium [34]. Pentabromopseudilin (20) is a highly active antibiotic and also shows anti-tumor and phytotoxic activity [34, 35]. Pentachloropseudilin (23) was first isolated from an Actinoplanes strain (ATCC 33002) [36]. Pentachloropseudilin (23) has a lower antibiotic potency than pentabromopseudilin (20). 

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