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Neue β-Lactam-Antibiotika. Zur Funktionalisierung von 3-Hydroxy-3-cephem-4-carbonsäureestern durch die Wittig-Reaktion. Modifikationen von Antibiotika. 16. Mitteilung [1]

✍ Scribed by Riccardo Scartazzini


Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
876 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis


New β‐lactam antibiotics. Functionalisation of 3‐hydroxy‐3‐cephem‐4‐carboxylic esters through the Wittig reaction

The 3‐hydroxy‐ceph‐3‐em‐esters 1a, b reacted smoothly with stabilized phosphor‐ylids to give a series of derivatives which were converted into the microbiologically active acids 14a, c, 15c and 20 by known procedures. The synthesis of the amides 23, 24, 26 and of the ester 28 from the 3‐carboxymethyl‐derivative 19 is also reported.


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Neue β-Lactam-Antibiotika. Über die Dars
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## Abstract Benzhydrylic esters of 3‐unsubstituted cephem‐4‐carboxylic acids of types **9** and **10** (__Scheme 2__) are prepared by decarbonylation of esters of 3‐formylcephem compounds of type **2** with tris‐triphenylphosphine‐rhodium chloride. The preparation of the starting materials **2** an

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## Abstract Oxydation of **2** with iodine followed by acylation leads to β‐lactamdisulfides of type **3**. Compounds **3** can be transformed into alcohols **4** by reductive alkylation with ethylenoxide and zinc/acetic acid. Compounds **4** are used as starting materials for the synthesis of N‐ac