The synthesis of <scp>D</scp>,<scp>L</scp>-cis-N-oxalamido-3-N-phenylacetamido-4-methoxy methyl-2-azetidinone

Just, George; Liak, T. J.

doi:10.1139/v78-033

Cited by 31 publications

(7 citation statements)

References 6 publications

(6 reference statements)

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“…We believe that the configuration at C(2) of the succinate moiety in p-lactams 14 and 16, with respect to C(2) of the corresponding precursors 9 and 13, was not retained duringp-lactam-ring formation. This was observed previously in a similar reaction in which L-serine was used as the starting material [9]. The cis-configuration in the p-lactams were determined by ,H-C(4)) = 5 Hz) of the derivatives, in which the relevant protons did not overlap with other signals [lo] [ll].…”

supporting

confidence: 60%

Syntheses of the First Selenium‐Containing Bicyclic β ‐Lactams as Potent Antimicrobial Agents

Hwu

Lai

Hakimelahi

et al. 1994

Helvetica Chimica Acta

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Syntheses of the cis-configurated isodethiaselenapenam 5 (Scheme 1 ) as well as the isodethiaselenacephems 29 and 31 (Scheme 2) were accomplished, in which the key step involved addition of Se to the corresponding carbanions of 1,25, and 27 followed by internal alkylation.8-Lactams 29 and 31 were found to possess biological activity against several pathogenic microorganisms in v i m . The electronic activation of the Iactam moiety in the isodethiaselenacephem 31 and the corresponding isocephem 33 remarkably enhanced their biological activity. Isodethiaselenacephem 31 was more toxic than isocephem 33 in experimental animals.Introduction. -Elemental sulfur reacts with phosphoryl carbanions to give phosphorylmethane thiols, which upon treatment with alkylating agents lead to phosphorylmethyl sulfides [l] [2]. In this connection, we found that the reaction of phosphoryl carbanions of monocyclicp-lactams (i.e. 1) with elemental sulfur gave the corresponding sulfido salts. These salts underwent an internal SN2 of the mesylate functionality to afford the corresponding bicyclic / l -1actams (e.g. 2) [3]. Herein, we report our findings on the exploration of the reaction of the phosphoryl carbanion of 1 and sulfonyl carbanions of 25 and 27 with elemental selenium. These reactions afford the corresponding isodethiaselenapenam 5 (Scheme 1) and isodethiaselenacephems 29 and 31 (Scheme 2). In addition, we report a new synthesis of biologically active isocephem 33 [4] (Scheme 2) by reaction of the sulfonyl carbanion of 27 with elemental sulfur.

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confidence: 60%

Syntheses of the First Selenium‐Containing Bicyclic β ‐Lactams as Potent Antimicrobial Agents

Hwu

Lai

Hakimelahi

et al. 1994

Helvetica Chimica Acta

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“…[15] azetidinones. Examples are the intermolecular carbene insertion of β-oxodiazo esters into the NH lactam bond, as catalyzed by Rh 2 (OAc) 4 , [6] the enolization of N-1,3-acetal esters by TFA, [7] and the generation of transient N-vinyl-2-azetidinones from β-lactams derived from amino esters, especially serine [8] and threonine, [9] 2-amino-1,3-propanediols, [10] allylamine, [11] and β-hydroxyamines. Different approaches to this type of 2-azetidinone derivative are known.…”

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confidence: 99%

A Three-Step General Synthesis of 2-Azetidinones Bearing N-Dehydroamino Acid Side Chains

Alcaide¹,

Polanco²,

Sierra³

1998

Eur. J. Org. Chem.

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An efficient, three-step synthesis of N-vinyl-2-azetidinones 7 selenylation, and finally m-CPBA treatment, afforded Nvinyl-2-azetidinones 7 in fair to excellent yields, with starting from α-or β-amino ester imines 4 has been developed. Staudinger reaction between imines 4 and a retention at the remaining stereocenters of the starting material. Two examples of the use of compounds 7 to prepare ketene precursor gave 2-azetidinones 5. Enolate formation on the amino ester moiety of the 2-azetidinone 5, bi-and tricyclic 2-azetidinones are presented. Introductionrived from α-or β-amino esters. Our approach is based on the sequential Staudinger reaction between a ketene precurThe increasing resistance of bacteria to commonly used sor and an amino ester imine, followed by α-selenylation of β-lactam antibiotics [1] and the ever-growing new appli-the amino ester moiety of the 2-azetidinone, and finally, cations of these products in fields ranging from enzyme in-oxidative deseleniation to produce the desired compounds. hibition [2] to the use of 2-azetidinones as raw materials for To the best of our knowledge, the sole precedent for the use developing new synthetic methodologies [3] have triggered a of a seleno derivative to prepare an N-vinyl-2-azetidinone renewed interest in developing new routes to polycyclic β-is the treatment of β-lactam 2, prepared by cycloaddition lactam systems. Our own interest in this field has resulted of azidoacetyl chloride to the imine 1, with m-CPBA/ in new approaches to the synthesis of bi-and polycyclic 2-iPr 2 NH to afford compound 3 (Scheme 1).

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“…Part; cf. [71]), and by comparison with 25. The 4,5-d-erthyro-configuration follows from the configuration of the imines (there is no evidence for epimerisation).…”

mentioning

confidence: 99%

β-Lactams fromD-Erythrose-Derived Imines: A Convenient Synthesis of 2,3-Diamino-2,3-dideoxy-D-mannonic-Acid Derivatives

Storz

Bernet

Vasella

1999

HCA

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The synthesis of D,L-cis-N-oxalamido-3-N-phenylacetamido-4-methoxy methyl-2-azetidinone

Abstract: The title compound γmax 1810 cm−1, has been synthesized in 18% yield, starting from L-serine.

Cited by 31 publications

References 6 publications

Syntheses of the First Selenium‐Containing Bicyclic β ‐Lactams as Potent Antimicrobial Agents

Syntheses of the First Selenium‐Containing Bicyclic β ‐Lactams as Potent Antimicrobial Agents

A Three-Step General Synthesis of 2-Azetidinones Bearing N-Dehydroamino Acid Side Chains

β-Lactams fromD-Erythrose-Derived Imines: A Convenient Synthesis of 2,3-Diamino-2,3-dideoxy-D-mannonic-Acid Derivatives

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