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Approaches to the synthesis of phosphorus analogues of the beta-lactam antibiotics. [PDF]

, 1982
Mickel, Stuart J.
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Formal synthesis of Thienamycin

The Journal of Antibiotics, 2017
A formal synthesis of Thienamycin from ethyl (E)-crotonate and a cyclic five-membered nitrone derived from 2-deoxy-d-ribose is described. The synthesis involves 1,3-dipolar cycloaddition, cleavage of the N-O bond in the adduct, and intramolecular N-acylation to afford a bicyclic carbapenam skeleton.
Michał, Pieczykolan, Bartłomiej, Furman, Marek, Chmielewski   +2 more
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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, H, Kropp, J G, Sundelof, J, Birnbaum   +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, D. B. R. JOHNSTON, B. G. CHRISTENSEN   +2 more
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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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A practical synthesis of (±)-thienamycin

Tetrahedron Letters, 1980
Abstract An efficient and operationally simple synthesis of (±)-thienamycin is described.
D.G. Melillo, I. Shinkai, T. Liu, K. Ryan, M. Sletzinger   +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, Jacob Mathew, M. Narayana Rao   +2 more
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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
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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, B, LeBlanc, S, Weaver, G P, Bodey   +3 more
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