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Thienamycin: development of imipenem-cilastatin

Journal of Antimicrobial Chemotherapy, 1983
Thienamycin, a natural product produced by Streptomyces cattleya is the first representative of a unique class of beta-lactam antibiotics, the carbapenems. Despite its outstanding potency and antibacterial spectrum, thienamycin was itself unsuited for further development because of its chemical instability in concentrated solution and in the solid ...
F M, Kahan   +3 more
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A comparative in vitro study of thienamycin

Infection, 1982
The in vitro activity of thienamycin was compared to that of other antibiotics against a large panel of bacteria obtained in blood cultures from cancer patients. This compound was the most active against gram-positive cocci and also proved to be extremely active against the gram-negative bacteria.
V, Fainstein   +3 more
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A practical synthesis of (±)-thienamycin

Tetrahedron Letters, 1980
Abstract An efficient and operationally simple synthesis of (±)-thienamycin is described.
D.G. Melillo   +4 more
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A formal synthesis of (±)-thienamycin

J. Chem. Soc., Chem. Commun., 1986
An α-silylethylidene-β-lactam is generated via chlorosulphonyl isocyanate (CSI) addition to a silylated allenyl sulphide and converted into a key intermediate for the synthesis of thienamycin.
John D. Buynak   +2 more
openaire   +1 more source

Thienamycin-imipenem

2000
Abstract Despite the outstanding antibacterial profile of thienamycin 1, this compound was not considered attractive for clinical use because of its high chemical instability, found to be both pH- and concentration-dependent.4.
Walter Cabri, Romano Di Fabio
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Total synthesis of thienamycin analogs. 1. Synthesis of the thienamycin nucleus and dl-decysteaminylthienamycin

Journal of the American Chemical Society, 1978
Ausgehend 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
openaire   +1 more source

Thienamycin. A solution of the stereochemical problem

Tetrahedron Letters, 1979
Abstract A new nitrone-based synthesis of β-lactams is described which makes provision for the 1-hydroxyethyl moiety in the potent antibiotic thienamycin. Moreover, the relative stereochemical features of the natural product are defined in a step involving the cycloaddition of a nitrone with methyl crotonate.
Joseph J. Tufariello   +3 more
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ChemInform Abstract: THIENAMYCIN TOTAL SYNTHESIS. 3. TOTAL SYNTHESIS OF (.+‐.)‐THIENAMYCIN AND (.+‐.)‐8‐EPITHIENAMYCIN

Chemischer Informationsdienst, 1980
AbstractAus dem früher aufgeführten sterisch definierten Azetidinon‐carbinol (I) entsteht der Aldehyd (II), der in das Dithioacetal (III) übergeführt wird und zu (IVa) eliminiert.
S. M. SCHMITT   +2 more
openaire   +1 more source

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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The Biosynthesis of Thienamycin and Related Carbapenems

Critical Reviews in Biotechnology, 1986
(1986). The Biosynthesis of Thienamycin and Related Carbapenems. Critical Reviews in Biotechnology: Vol. 4, No. 1, pp. 111-131.
Joanne M. Williamson, Gene M. Brown
openaire   +1 more source

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