Showing papers on "Thienamycin published in 1988"
TL;DR: Optically pure 4-acetoxy-3-[1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone( 1b ), which is a highly versatile intermediate for the synthesis of thienamycin( 2 ) and other biologically active [β-lactam analogs, was synthesized from 4-carboxy-3 [1-( t-buyldimmethylsily loxy) methyl]-2.
46 citations
TL;DR: The complete stereoselective synthesis of (3R,4R)-3-[(S)-1′-hydroxyethyl]-4-phenylethynyl-2-azetidinone and its 4-phenyethenyl derivative were accomplished by the reaction of the organozinc derivative of (R)-methyl-3-hydroxbutyrate with N-trimethylsilylimines as mentioned in this paper.
Abstract: The complete stereoselective synthesis of (3R,4R)-3-[(S)-1′-hydroxyethyl]-4-phenylethynyl-2-azetidinone and its 4-phenyethenyl derivative were accomplished by the reaction of the organozinc derivative of (R)-methyl-3-hydroxybutyrate with N-trimethylsilylimines.
22 citations
TL;DR: In this paper, an enantio and diastereoselective route to β-lactam synthons has been developed; two novel key radical reactions allowed them to obtain two useful intermediates in the synthesis of thienamycin and PS-5.
22 citations
03 Nov 1988
TL;DR: The π-allytricarbonyliron lactones with amines were used in the formal total synthesis of nocardicins and ( + )-thienamycin this paper.
Abstract: π-Ally tricarbonyliron lactone complexes are useful precursors for organic synthesis. These stable complexes are readily prepared from a variety of organic substrates and may be respectively converted to β- and δ-lactones by selective oxidation or exhaustive carbonylation. The natural products massoialactone, parasorbic acid, the carpenter bee pheromone and malyngolide were prepared by using the iron carbonyl methodology, along with precursors for the ionophore antibiotic CP 61405 and avermectin B1a synthesis. Several corresponding lactam complexes were obtained by treatm ent of the π-allytricarbonyliron lactones with amines in the presence of Lewis acids. These complexes were used in the formal total synthesis of the nocardicins and ( + )-thienamycin.
19 citations
TL;DR: In this article, a key intermediate to thienamycin is synthesized enantioselectively under complete stereo and regio-chemical control starting from a chiral half ester 5 enzymatically generated.
18 citations
TL;DR: Methionine interference in the formation of thienamycin byStreptomyces cattleya is due, to a major extent, to inhibition of enzyme activity.
Abstract: Methionine interference in the formation of thienamycin byStreptomyces cattleya is due, to a major extent, to inhibition of enzyme activity.
13 citations
TL;DR: In this article, a base-catalysed isoxazole-oxazone ring transformation was realized in the conversion of ethyl 5-hydroxy-3-(5-methylisoxazol-4-yl) isoxozone-4 carboxylate into 4-cyano-5methyloxazoxone-2-ylacetic acid.
Abstract: A novel base-catalysed isoxazole-oxazole ring transformation was realized in the conversion of ethyl 5-hydroxy-3-(5-methylisoxazol-4-yl) isoxazole-4-carboxylate into 4-cyano-5-methyloxazol-2-ylacetic acid. A new process was developed for the preparation of t-4-amino-c-2-methyl-6-oxotetrahydropyran-r-3-carboxylic acid hydrochloride, a starting material for the synthesis of thienamycin.
12 citations
TL;DR: The generation of reactive carbenoid intermediates by transition metal-catalyzed decomposition of α-diazo carbonyl compounds is a rapidly developing area of synthtic methodology as mentioned in this paper.
10 citations
TL;DR: Computerassisted simulation using the rate constants revealed that there is an upper limit to the extents of inactivation by imipenem and thienamycin.
Abstract: The mechanism of inhibition of type Ib penicillinase by imipenem (N-formimidoyl thienamycin) and thienamycin was studied. Imipenem and thienamycin. were found to inhibit the penicillinase in a progressive manner, but they differed from one another in the maximum level of enzyme inhibition, even with excess inhibitor. The maximum inhibitions by imipenem and thienamycin amounted to about 50% and 80%, respectively. To elucidate the mechanism of the equilibrium phenomenon, the rate constants in the proposed scheme were estimated. Computerassisted simulation using the rate constants revealed that there is an upper limit to the extents of inactivation by imipenem and thienamycin.
3 citations
Journal Article•
TL;DR: Both cefazolin and thienamycin were of the same value in cases of lung resections, while thien amycin was clearly superior in resections of thoracic oesophagus.
Abstract: A comparison was made of the use of thienamycin and cefazolin in antimicrobial prophylaxis of patients undergoing major thoracic noncardiac surgery. Fever and failure or success of prophylaxis were used as criteria. Both cefazolin and thienamycin were of the same value in cases of lung resections, while thienamycin was clearly superior in resections of thoracic oesophagus.
1 citations
TL;DR: The generation of reactive carbenoid intermediates by transition metal-catalyzed decomposition of α-diazo carbonyl compounds is a rapidly developing area of synthtic methodology.
Abstract: The generation of reactive carbenoid intermediates by transition metal-catalyzed decomposition of α -diazo carbonyl compounds is a rapidly developing area of synthtic methodology. Addition of such species to olefins affords cyclopropane-carboxylate esters such as 1 which has been widely used in organic synthesis 1 and synthetic pyrethroid insecticides 2. Moreover, addition of such carbenoids to C-H and N-H bonds provides stereocontrolled access to products ranging from steroids3 to thienamycin derivatives 4.
TL;DR: In this article, the enantiomeric 4-acetoxy-2-azetidinone (5 ) with the 2-siloxy-1,3-butadiene (8 ) gives the carbacephem 9 which is cleaved via ozone and cyclized to the carbapenem system (+)- 13 in 30% overall yield.
Abstract: Cycloaddition of the enantiomeric 4-acetoxy-2-azetidinone ( 5 ) with the 2-siloxy-1,3-butadiene ( 8 ) gives the carbacephem 9 which is cleaved via ozone and cyclized to the carbapenem system (+)- 13 in 30% overall yield.
TL;DR: In this paper, a base-catalysed isoxazole-oxazone ring transformation was realized in the conversion of ethyl 5-hydroxy-3-(5-methylisoxazol-4-yl) isoxozone-4 carboxylate into 4-cyano-5methyloxazoxone-2-ylacetic acid.
Abstract: A novel base-catalysed isoxazole-oxazole ring transformation was realized in the conversion of ethyl 5-hydroxy-3-(5-methylisoxazol-4-yl) isoxazole-4-carboxylate into 4-cyano-5-methyloxazol-2-ylacetic acid. A new process was developed for the preparation of t-4-amino-c-2-methyl-6-oxotetrahydropyran-r-3-carboxylic acid hydrochloride, a starting material for the synthesis of thienamycin.
TL;DR: In this paper, a stereo and enantio-controlled synthesis of azetidinone from ethyl (S)-3-hydroxybutyrate is reported, where a simple method of inversion and concomitant protection of the hydroxy function in the side chain is achieved.
Abstract: Atotal stereo- and enantio-controlled synthesis of (3S,4R)-4-acetoxy-3-[(R)-1-hydroxyethyl]azetidin-2-one (1) from ethyl (S)-3-hydroxybutyrate is reported. A simple method of inversion and concomitant protection of the hydroxy function in the side chain is achieved. The synthesis starts with the conversion of ethyl (S)-3-hydroxybutyrate into the azetidinone derivatives (4) and (5)via a stereospecific imine-ester enolate cycloaddition. The resulting azetidinones, with unnatural configuration at C-l′ of the ethyl group were converted into the mesylates (8) and (9); these were further elaborated into the nitrate esters (10) and (11) with the natural configuration at C-1′. Sequential treatments of these compounds, with ozone, Jones' reagent, lead tetra-acetate, and cerium ammonium nitrate afforded as a sole product, in 24.8% overall yield, the chiral azetidinone (17). Finally, smooth removal of the nitric protecting group of the hydroxy function afforded, quantitatively, the azetidinone (1), a key intermediate for the preparation of thienamycin and its biologically active analogues.