The total synthesis of chiral ~~4,7-lactam1~ 4 has been accomplished starting from &acetoxyazetidinone. An independent route from methyl penicillanate has been used to test the efficiency of the foregoing synthesis. We recently reported (1) the skeletal conversion of penicillanic acid to (+)-2,2,5,
Free-radical annelation in the synthesis of bicyclic β-lactams. 1. Synthesis of 8-oxo-5-oxa-1-azabicyclo[4.2.0]octane and 9-oxo-6-oxa-1-azabicyclo[5.2.0]nonane derivatives
✍ Scribed by Mario D. Bachi; Christian Hoornaert
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 199 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A new method for the synthesis of some fused bicyclic B-lactams based on the completion of the molecular backbone by a free-radical C-C bond forming reaction is described. Many of the synthetic approaches to the fused bicyclic molecular backbone of B-lactam antibiotics are based on the annelation of non-fused B-lactams bearing the appropriate appendages. 192 3 In most cases this transformation is performed by a ionic-reaction. Considering the high sensi-
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## Abstract Ethyl 4‐oxoalkanoates 1 react at ambient temperature in dry methanol in the presence of molecular sieve 3 Å in almost quantitative yield with 3‐aminopropanol and 2‐aminoethanol to form the bicyclic lactams __rac__‐2 and __rac__‐3, respectively. Surprisingly, the (±)‐5‐alkyl‐4‐oxa‐1‐azab
The synthesis of a d'carbapenem and two ,?-lactams possessing a Br-atom at the N-substituting center not involved in the lactam ring and bearing the carboxyl group is described. The ,?-lactams having this kind of Br-substitution are more susceptible to nucleophilic attack than those having a conjuga