Pyoluteorin, a synthesis

Abstract

The synthesis of Pyoluteorin, an antibiotic from Pseudomonas aeruginosa is described. The method used produced in addition, an isomer 3,5-dichloro-2-(2',6'-dihydroxybenzoyl)pyrrole, for which the name isopyolrrteoritt is proposed. The bromine analogue of pyoluteorin is also reported.

Nitro analogs of pyoluteorins

“…In the present investigation, two modes of modification of 2a were chosen in an effort to obtain reduced toxicity: (a) insertion of a substituent, preferably a bulky one, on the N' nitrogen and (b) attaching a group at the hydroxyl which would be less susceptible to hydrolysis than 2b. Compounds [5][6][7][8][9][10][11][12][13] (Table I) are representative of the former approach while 14 and 15 are examples of the latter.…”

High-Efficiency Synthesis of Carbon-Bridged Dimers via Bioinspired Green Dimerization Involving Aldehydes

“…aeruginosa 1682U.R.0a.27, with formaldehyde, and this process was spontaneous. To confirm our deduction, we synthesized pyoluteorin ( 12 ) in four steps and 38% overall yield on gram scale, − which was further treated with formaldehyde to yield mindapyrrole A ( 9 ) (Scheme ). When the mixture of 12 and formaldehyde was stirred in pure water at rt, only traces of the product were observed.…”

The Chlorination of Pyrroles. Part II

“…Byreactionofl(X=Y = C l ; Z = H ; R = N a ) with 6 (x = 1) we obtained a pure sample of 8 (3) and hence of pyoluteorin.…”

“…Didechloro-0,O'-dimethylpyoluteorin, 80 mg, was treated with boron trichloride as described (3). The product, after crystallization from benzenellight petroleum, had m.p.…”

“…We found during the synthesis of pyoluteorin (2,3) that the preparation (4) of pure 4,5-dichloropyrrole-2-carboxylate was troublesome. We therefore prepared pyrryl-2-glyoxylyl chloride (1, X = Y = Z = H ; R = C1) (5) and hence the acid (1, X = Y = Z = H ; R = OH) and its isobutylamide 2.…”