2009
DOI: 10.1002/ejoc.200801193
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Novel Large‐Ring 1,3‐Bridged 2‐Azetidinones as Potential Inhibitors of Penicillin‐Binding Proteins

Abstract: a b s t r a c tThe relationship between angular strain and (re)activity of bicyclic 2-azetidinones is still an open question of major concern in the field of penicillin antibiotics. Our study deals with original 13-membered-ring 1,3-bridged 2-azetidinones related to the carbapenem family, and featuring a ''planar amide'' instead of the ''twisted amide'' typical of penam derivatives. The bicycles 11 and 12 were obtained from acetoxy-azetidinone 7, via the key-intermediate 10, by using the RCM (ring closing meta… Show more

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Cited by 22 publications
(11 citation statements)
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“…The co-existence of conformers remained to be proved by experimental methods. Conformers were detected by 1 H-NMR, only in the case of one monocyclic 2-azetidinone precursor of RCM cyclization [4]. Here, the occurrence of conformers is demonstrated in the case of one bicyclic 2-azetidinone by X-ray diffraction analysis.…”
mentioning
confidence: 78%
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“…The co-existence of conformers remained to be proved by experimental methods. Conformers were detected by 1 H-NMR, only in the case of one monocyclic 2-azetidinone precursor of RCM cyclization [4]. Here, the occurrence of conformers is demonstrated in the case of one bicyclic 2-azetidinone by X-ray diffraction analysis.…”
mentioning
confidence: 78%
“…The title compound was prepared in five steps from (3S,4R)-3-[1(R)-t-butyldimethylsilyloxy)-ethyl]-4-(propyl)-2-azetidinone as described in [1]. Crystallization from aceton/ether mixture (v/v,1:2) gave white crystals suitable for X-ray diffraction analysis (m.p.…”
Section: Source Of Materialsmentioning
confidence: 99%
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“…159 A series of bicyclic 1,3-bridged-2-azetidinones (66 as a representative structure), which have been demonstrated to be inhibitors of penicillin-binding proteins, represents another novel macrocyclic structural class accessed by RCM methodology. [160][161][162] Interestingly, both monomer and dimer-derived structures obtained from these latter efforts have been found to have utility. The steric and conformational constraints imposed by the bicyclic structures made RCM difficult in a number of cases.…”
Section: Ring-closing Metathesismentioning
confidence: 97%