The penems, a new class of .beta.-lactam antibiotics: 6-acylaminopenem-3-carboxylic acids

Ernest, I.; Gosteli, J.; Greengrass, C. W.; Holick, W.; Pfaendler, H. R.; Woodward, R. B.

doi:10.1021/ja00494a032

Cited by 164 publications

(30 citation statements)

References 2 publications

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“…7 Ylides 2 have been applied in Woodward's synthesis of β-lactam antibiotics since 1978. 8 At the present time, α-(dialkoxyphosphoryl)glycinates derived from β-lactams 4 are being used for this purpose. α-(Dialkoxyphosphoryl)glycinates 3 have been gaining importance since 1973, when they were used for the first time by Ratcliffe and Christensen for the synthesis of β-lactam antibiotics.…”

Section: Figurementioning

confidence: 99%

“…The discussed ylides are widely used for the synthesis of bicyclic β-lactam antibiotics. One of the earliest methods of synthesizing them, described by Woodward, consists in the treatment of the corresponding β-lactams 14 with glyoxylic acid esters [17][18][19][20][21][22] or their hemiacetals, 8,23,24 which yields the corresponding α-hydroxyglycine derivatives 15. The latter compounds react with thionyl chloride, followed by their reaction with triphenylphosphine in the presence of bases.…”

Section: Figurementioning

confidence: 99%

“…The latter compounds react with thionyl chloride, followed by their reaction with triphenylphosphine in the presence of bases. β-Lactam antibiotics 16 derived from penem-3-carboxylic acid (Z = S) 8,19,23,24 and carbapenem-2-carboxylic acid (Z = CH) 21 were synthesized using this method (Scheme 6). …”

Section: Figurementioning

confidence: 99%

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α-Amino acid derivatives with a Cα-P bond in organic synthesis

Mazurkiewicz¹,

Kuźnik²,

Grymel³

et al. 2007

Arkivoc

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α-Amino acid derivatives with a C α -P bond have been used for a wide range of chemical transformations, including synthesis of many kinds of bioactive compounds, e.g. nonproteinogenic α-amino acids, α,β-dehydro-α-amino acids, dehydropeptides, β-lactam antibiotics and glycopeptides. The present review is focused on methods of synthesis of the title compounds, their properties and application in organic synthesis.

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Section: Figurementioning

confidence: 99%

Section: Figurementioning

confidence: 99%

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α-Amino acid derivatives with a Cα-P bond in organic synthesis

Mazurkiewicz¹,

Kuźnik²,

Grymel³

et al. 2007

Arkivoc

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show abstract

“…Soon afterwards (Fig. 7), Woodward's synthesis of penems (23), and the discovery of thienamycin (24), clavulanic acid (25), the nocardicins (26), and the monobactams (27) attracted many more workers to the field. One of these groups was directed by Wataru Nagata at the S 0111: time ago: I pul~lisl~erl n r~lethot!…”

Section: Penicillin Binding Proteins (Pbp's)mentioning

confidence: 99%

1992 Lemieux Award Lecture Studies related to the penicillin receptor

Wolfe¹

1994

Can. J. Chem.

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The relative antibacterial activities of penicillins and cephalosporins are discussed in terms of their differing abilities to complex to and react with penicillin-binding proteins. The insights gained from such an analysis are being used to attempt the design of new kinds of structures targeted to the penicillin receptor. Details of such design, and examples of several new classes of compounds suggested by this work, are described. Some of these compounds exhibit interesting antibacterial activity.

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“…Sodium n-propyl trithiocarbonate, prepared by addition of carbon disulfide to a methanolic sodium n-propylmercaptide solution, was treated with a stoichiometric amount of 4-acetoxyazetidin-2-one5) at room temperature to give the azetidinone trithiocarbonate* (4a) as fine yellow needles, nip 79-80°C (74% yield): IR (Nujol) 3210, 1759 cm-1; NMR 1 (CDCl3+D2O) 1 ). The carboxylic acid (5b) was obtained as its sodium salt (powder) by shaking 5a in hydrogen atmosphere over 10 % palladium on charcoal in a buffer solution (pH 7) and was submitted to biological test.…”

Section: Synthesis Of Penems and Their Antibacterial Activitiesmentioning

confidence: 99%