A Versatile Strategy for the Solid-Phase Synthesis of Penicillin Derivatives: Efficient Preparation of 2β-Methyl Substituted Penams as β-Lactamase Inhibitor Analogues

Abstract A convenient solid-phase method for the synthesis of 2β-methyl substituted penicillins using commercially available resins is described. Functionalization of Merrifield and Wang resin bound penam derivatives was performed by penicillin sulfoxide rearrangement and the products were released...

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Veröffentlicht in:Synthesis (Stuttgart) 2006-10, Vol.2006 (20), p.3397-3404
Hauptverfasser: Boggián, Dora B., Mata, Ernesto G.
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract A convenient solid-phase method for the synthesis of 2β-methyl substituted penicillins using commercially available resins is described. Functionalization of Merrifield and Wang resin bound penam derivatives was performed by penicillin sulfoxide rearrangement and the products were released from the supports under mild conditions. The utility of this methodology has been demonstrated by synthesizing a small library of penicillin derivatives in moderate to very good overall isolated yields for the multistep synthetic sequence.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-950214