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Issue 0, 1984
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Clavulanic acid and its derivatives. Structure elucidation of clavulanic acid and the preparation of dihydroclavulanic acid, isoclavulanic acid, esters and related oxidation products

Abstract

Clavulanic acid, a novel β-lactamase inhibitor from Streptomyces clavuligerus, has been shown to be Z-(2R,5R)-3-(β-hydroxyethylidene)-7-oxo-4-oxa-1 -azabicyclo[3.2.0]heptane-2-carboxylic acid (1). The structure and absolute stereochemistry was confirmed by X-ray analysis of the p-nitrobenzyl and p-bromobenzyl esters, (14) and (15). The conversion of clavulanic acid into a variety of esters and acyl derivatives is described. An account of its isomerisation to the E isomer (30) and the formation of an oxetane (45) as a by-product of the photolysis of the phenacyl ester (18) is given. The reduction and oxidation of acid (1) under a variety of conditions has also been examined in detail.

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Article type: Paper
DOI: 10.1039/P19840000635
Citation: J. Chem. Soc., Perkin Trans. 1, 1984, 635-650
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    Clavulanic acid and its derivatives. Structure elucidation of clavulanic acid and the preparation of dihydroclavulanic acid, isoclavulanic acid, esters and related oxidation products

    A. G. Brown, D. F. Corbett, J. Goodacre, J. B. Harbridge, T. T. Howarth, R. J. Ponsford, I. Stirling and T. J. King, J. Chem. Soc., Perkin Trans. 1, 1984, 635
    DOI: 10.1039/P19840000635

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