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Neue β-Lactam-Antibiotika. Über die Darstellung der 8-β-Phenylacetamido-homoceph-4-em-5-carbonsäure (1). Modifikationen von Antibiotika, 7. Mitteilung

✍ Scribed by R. Scartazzini; J. Gosteli; H. Bickel; R. B. Woodward

Publisher: John Wiley and Sons
Year: 1972
Tongue: German
Weight: 409 KB
Volume: 55
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19720550734

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✦ Synopsis

Abstract

The thiazolidine β‐lactam 3 adds acrolein in a Michael type reaction. The resulting 'carbinolamide 4 is converted to 8‐β‐phenylacetamido‐homoceph‐4‐em‐5‐carboxylic acid (1) by previously described methods.

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✍ R. Scartazzini; H. Bickel 📂 Article 📅 1972 🏛 John Wiley and Sons 🌐 German ⚖ 496 KB 👁 1 views

## 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