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Synthesis and Biological Evaluation of Functionalized Epoxides Structurally Related To the Carbapenem Family

Marchand-Brynaert, Jacqueline;Davies, J.;Ghosez, Léon
(1992) Heterocycles — Vol. 33, n° 1, p. 313-326 (1992)

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  • Marchand-Brynaert, JacquelineUCLouvain
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  • Davies, J.
    Author
  • Ghosez, LéonUCLouvain
    Author
Abstract
Epoxides (6) and (7), topologically related to the carbapenem antibiotics, were designed as potential alkylating inhibitors of the bacterial D,D-peptidases. The olefinic precursors (8-9) were readily prepared, in three steps, by coupling the Wittig reagent (13) with the aldehyde synthons (10) or (11) resulting from diastereoselective aldol condensations. Epoxide (7) showed a weak anti-beta-lactamase activity.
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Marchand-Brynaert, J., Davies, J., & Ghosez, L. (1992). Synthesis and Biological Evaluation of Functionalized Epoxides Structurally Related To the Carbapenem Family. Heterocycles, 33(1), 313-326. https://doi.org/10.3987/COM-91-S40 (Original work published 1992)