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Total synthesis of thienamycin analogs. II Synthesis of 2-alkyl and 2-aryl thienamycin nuclei

Tetrahedron Letters, 1980
Abstract A new general synthesis leading to 2-alkyl and 2-aryl-1-carba-2-penem-3-carboxylic acids involves the preparation of a key thiolester intermediate 3. This is reacted with Me2CuLi or (C6H5)2MgCuX to give the corresponding methyl or phenyl ketone which undergoes a Wittig reaction to give the desired penems, which can be deblocked ...
L. Cama, B.G. Christensen
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An enantioselective formal synthesis of thienamycin

Tetrahedron Letters
Thienamycin is a carbapenem antibiotic with potent activity against gram-negative and gram-positive bacteria. Due to its promising activity but lack of chemical stability, thienamycin serves as inspiration for new synthetic antibiotic scaffolds. In this study, we report a nine-step enantioselective formal synthesis of thienamycin. Our route utilizes an
Jamie L. Breunig   +2 more
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Preparation and antibacterial activity of .DELTA.1-thienamycin

Journal of Medicinal Chemistry, 1981
delta 1-Thienamycin (2), a double-bond isomer of thienamycin, was prepared by isomerizing N-[[(p-nitrobenzyl)oxy]-carbonyl]thienamycin p-nitrobenzyl ester (5b) with DBU in Me2SO followed by hydrogenolysis of the protecting groups. When evaluated in a disc-diffusion antibacterial assay, delta 1-thienamycin was found to be essentially devoid of activity.
D H, Shih, R W, Ratcliffe
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ChemInform Abstract: Asymmetric Synthesis of (+)‐Thienamycin.

Chemischer Informationsdienst, 1983
AbstractEs wird ein Syntheseweg angegeben für die Umwandlung des Propargyl‐azetidinons (I) zum Thienamycin‐Vorprodukt (II).
M. SHIBASAKI, A. NISHIDA, S. IKEGAMI
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Continuous production of thienamycin in immobilized cell systems

Biotechnology and Bioengineering, 1986
AbstractA novel 2‐L bubble column was used to study the continuous, immobilized cell production of thienamycin. Cells of Streptomyces cattleya were immobilized by culturing them in an appropriate growth medium containing 60/80 mesh celite particles. The dilution rate used during the continuous growth phase was 0.2 h−1.
E J, Arcuri, G, Slaff, R, Greasham
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ChemInform Abstract: TOTAL SYNTHESIS OF (.+‐.)‐THIENAMYCIN

Chemischer Informationsdienst, 1978
AbstractDas aus 1‐Acetoxy‐butadien mit Chlorsulfonylisocyanat erhaltene Acetidinon (Ia) gibt bei reduktiver Hydrolyse (H2O, K,HPO4, Na,SO3, 0°C) (Ib) (42% Gesamtausb.).
D. B. R. JOHNSTON   +3 more
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A stereocontrolled, enantiomerically specific total synthesis of thienamycin

Philosophical Transactions of the Royal Society of London. B, Biological Sciences, 1980
A versatile stereocontrolled total synthesis of thienamycin starting from L-aspartic acid is reported. Stereocontrol is achieved by potassium tri- sec -butylborohydride reduction of a thermodynamically formed 3α-acetylazetidinone intermediate.
T N, Salzmann   +3 more
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ChemInform Abstract: TOTAL SYNTHESIS OF THIENAMYCIN ANALOGS. 1. SYNTHESIS OF THE THIENAMYCIN NUCLEUS AND DL‐DECYSTEAMINYLTHIENAMYCIN

Chemischer Informationsdienst, 1979
AbstractAusgehend von dem Azetidinon (I) bzw. dem Oxaazabicyclooctanon (Va) wird das Carbapenem‐carboxylat (IVb) bzw. das dl‐Descysteaminylthienamycinsalz dl‐(VIIIb) synthetisiert.
L. D. CAMA, B. G. CHRISTENSEN
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ChemInform Abstract: THIENAMYCIN TOTAL SYNTHESIS. 1. SYNTHESIS OF AZETIDINONE PRECURSORS OF (.+‐.)‐THIENAMYCIN AND ITS STEREOISOMERS

Chemischer Informationsdienst, 1980
AbstractIm Zusammenhang mit der Synthese des antibiotisch wirksamen Thienamycins (XIV) werden verschiedene Modellreaktionen beschrieben.
F. A. BOUFFARD   +2 more
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Antibacterial Activity of Imipenem: The First Thienamycin Antibiotic

Clinical Infectious Diseases, 1985
Imipenem (N-formimidoyl thienamycin) is the first representative of a new class of beta-lactam antibiotics--the carbapenems. Imipenem has an unusually broad spectrum, high potency, and no cross-resistance with other beta-lactam antibiotics. Susceptible gram-negative species include Pseudomonas aeruginosa, Serratia, and Enterobacter.
H, Kropp   +3 more
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