β-Lactams from Carbohydrates

Furman, Bartłomiej; Kałuża, Zbigniew; Stencel, Agnieszka; Grzeszczyk, Barbara; Chmielewski, Marek

doi:10.1007/7081_2006_046

Cited by 12 publications

(3 citation statements)

References 136 publications

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“…These tend to offer, however, a poor yield of the bicyclic β-lactams . In connection with our interest in the synthesis of β-lactams, as well as in the 1,3-dipolar cycloadditions involving cyclic nitrones, we decided to investigate, for the first time, a general and a highly stereoselective approach to the construction of the carbapenams basic skeleton, using Cu(I)-mediated cycloaddition of nonracemic nitrones and simple acetylenes (Scheme ).…”

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confidence: 99%

Diastereoselective Synthesis of Carbapenams via Kinugasa Reaction

et al. 2008

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confidence: 99%

Diastereoselective Synthesis of Carbapenams via Kinugasa Reaction

et al. 2008

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“…The route does not require any chiral auxiliary or catalyst, since the high enantioselectivity which is obtained is solely directed by the configuration of 2-chloroalkanoyl substituent. This also permits different configurations of A survey of the literature reports regarding the synthesis of b-lactam using carbohydrate precursors has recently been published by Furman et al [215]. They have shown that the carbohydrates were used either as chiral tools or chiral auxiliaries.…”

Section: Other Solid-phase Synthetic Approaches To B-lactamsmentioning

confidence: 97%

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

Mandal

Ghosh

Basu

2010

Heterocyclic Scaffolds I

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Since the discovery of penicillin in 1929, b-lactam antibiotics have been recognized as potentially chemotherapeutic drugs of incomparable effectiveness, conjugating a broad spectrum of activity with very low toxicity. The primary motif azetidin-2-one ring (b-lactam) has been considered as specific pharmacophores and scaffolds. With the advent of combinatorial chemistry and automated parallel synthesis coupled with ample interests from the pharmaceutical industries, recent trends have been driven mostly by adopting solid phase techniques and polymersupported synthesis of b-lactams. The present survey will present an overview of the developments on the polymer-supported and solid phase techniques for the preparation of b-lactam ring or b-lactam containing antibiotics published over the last decade. Both unsubstituted and substitutions with different functional groups at various positions of b-lactams have been synthesized using solid phase technology. However, Wang resin and application of Staudinger [2+2] cycloaddition reaction have remained hitherto the major choice. It may be expected that other solid phase approaches involving different resins would be developed in the coming years.

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“…Among numerous direct methodologies leading to the chiral β-lactams, , the Cu(I)-mediated cycloaddition/rearrangement cascade process of nitrones with terminal alkynes that proceeds in the presence of base (known as Kinugasa reaction) has received increased attention during the past decade. , …”

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A Formal Synthesis of Ezetimibe via Cycloaddition/Rearrangement Cascade Reaction

et al. 2011

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A formal synthesis of a powerful cholesterol inhibitor, ezetymibe 1, is described. The crucial step of the synthesis is based on Cu(I)-mediated Kinugasa cycloaddition/rearrangement cascade reaction between terminal acetylene derived from acetonide of L-glyceraldehyde and suitable C,N-diarylnitrone. The adduct with (3R,4S) configuration at the azetidinone ring, obtained with high stereoselectivity, was subsequently subjected to deprotection of the diol side chain followed by glycolic cleavage and base-induced isomerization at the C3 carbon atom to afford the (3S,4S) aldehyde, which has been already transformed into ezetimibe by the Schering-Plough group.

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β-Lactams from Carbohydrates

Cited by 12 publications

References 136 publications

Diastereoselective Synthesis of Carbapenams via Kinugasa Reaction

Diastereoselective Synthesis of Carbapenams via Kinugasa Reaction

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

A Formal Synthesis of Ezetimibe via Cycloaddition/Rearrangement Cascade Reaction

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