The total syntheses of the (+/-)-1-carba analogues of cefoxitin (11), 7 alpha-methoxydeacetylcephalothin (5) and cefamandole (31) and the (+/-)-1-oxa analogue of cefamandole (43) are described. Their bioactivity spectra against 14 typical organisms are similar to those of their natural 1-thia counterparts, with the 1-carba compounds somewhat less active and the 1-oxa compound more active than the natural ones.
Der aus (I) und (II) in Gegenwart von Natrium hergestellte Malonsäureester (III) reagiert nach Überführung in die Natrium‐Verbindung mit n‐Heptylbromid (IV) zu (V).
Das Benzophenon (I) bildet mit den Aminen (II) in Gegenwart von Zinkchlorid als Kondensationsmittel die Ketoanile (III), die sich als Chelatisierungsmittel für Kupfer(II), Nickel(II) und Kobalt(II) eignen.
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