Clavulanic acid. Rearrangement to 3, 4-disubstituted pyrroles

✍ Scribed by J.Sydney Davies; T.Trefor Howarth

• Book ID: 104221017
• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 200 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87546-2

✦ Synopsis

The methanolysis of clavulanic acid (2) end subsequent base catalysed rearrangement to 3, 4-disubstituted pyrroles is described.

Reports from these laboratoriesA have described the isolation and structural elucidation of olavulanic acid (2), a potent B-lactemase inhibitor produced by Streptomyces ClavuliRerus.

Subsequently, a progremme was initiated to investigate the primary and secondary processes involved in the degradation of olavulenic acid (2). We now report the facile rearrangement of clavulenic acid $0 3, 4-disubstituted pyrroles which share structural similarities with Verrucerin E (7), an antimitotic agent isolated from Myrothecium verrucaria 3 .