Simple and condensed β-lactams. Part 5. The synthesis of some (5RS,6SR)-2-(2-formylaminoethylthio)-6-(2-methyl-1,3-dioxolan-2-yl) carbapenem-3-carboxylic acid derivatives and related compounds

J. Fetter, Károly Lempert, Tibor Gizur, József Nyitrai, M. Kajtár-Peredy, Gyula Simig, Gyula Hornyák, Gábor Doleschall

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14 Citations (Scopus)

Abstract

Starting with the 4-oxoazetidine-2-carboxylic acids (3a) and (3b), methods for the synthesis of derivatives of the racemic carbapenem-3-carboxylic acid (2), an analogue of the potent antibiotic thienamycin have been developed. The synthetic steps included chain elongations by the methods of Arndt-Eistert and Masamune, diazo group transfers, oxidative removals of N-protecting 2,4-dimethoxybenzyl and p-methoxyphenyl groups, cyclization involving a carbene insertion reaction, and conversion of the ketone moiety of the bicyclic compound (13b) into an enethiol moiety via enolphosphate activation. The target compound, the sodium salt (14c) did not possess any useful biological activity.

Original languageEnglish
Pages (from-to)221-227
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1986

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Thienamycins
Sodium Compounds
Lactams
Cyclization
Carboxylic Acids
Bioactivity
Ketones
Elongation
Salts
Chemical activation
Derivatives
carbapenem-3-carboxylic acid
carbene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Simple and condensed β-lactams. Part 5. The synthesis of some (5RS,6SR)-2-(2-formylaminoethylthio)-6-(2-methyl-1,3-dioxolan-2-yl) carbapenem-3-carboxylic acid derivatives and related compounds",
abstract = "Starting with the 4-oxoazetidine-2-carboxylic acids (3a) and (3b), methods for the synthesis of derivatives of the racemic carbapenem-3-carboxylic acid (2), an analogue of the potent antibiotic thienamycin have been developed. The synthetic steps included chain elongations by the methods of Arndt-Eistert and Masamune, diazo group transfers, oxidative removals of N-protecting 2,4-dimethoxybenzyl and p-methoxyphenyl groups, cyclization involving a carbene insertion reaction, and conversion of the ketone moiety of the bicyclic compound (13b) into an enethiol moiety via enolphosphate activation. The target compound, the sodium salt (14c) did not possess any useful biological activity.",
author = "J. Fetter and K{\'a}roly Lempert and Tibor Gizur and J{\'o}zsef Nyitrai and M. Kajt{\'a}r-Peredy and Gyula Simig and Gyula Horny{\'a}k and G{\'a}bor Doleschall",
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pages = "221--227",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
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T1 - Simple and condensed β-lactams. Part 5. The synthesis of some (5RS,6SR)-2-(2-formylaminoethylthio)-6-(2-methyl-1,3-dioxolan-2-yl) carbapenem-3-carboxylic acid derivatives and related compounds

AU - Fetter, J.

AU - Lempert, Károly

AU - Gizur, Tibor

AU - Nyitrai, József

AU - Kajtár-Peredy, M.

AU - Simig, Gyula

AU - Hornyák, Gyula

AU - Doleschall, Gábor

PY - 1986

Y1 - 1986

N2 - Starting with the 4-oxoazetidine-2-carboxylic acids (3a) and (3b), methods for the synthesis of derivatives of the racemic carbapenem-3-carboxylic acid (2), an analogue of the potent antibiotic thienamycin have been developed. The synthetic steps included chain elongations by the methods of Arndt-Eistert and Masamune, diazo group transfers, oxidative removals of N-protecting 2,4-dimethoxybenzyl and p-methoxyphenyl groups, cyclization involving a carbene insertion reaction, and conversion of the ketone moiety of the bicyclic compound (13b) into an enethiol moiety via enolphosphate activation. The target compound, the sodium salt (14c) did not possess any useful biological activity.

AB - Starting with the 4-oxoazetidine-2-carboxylic acids (3a) and (3b), methods for the synthesis of derivatives of the racemic carbapenem-3-carboxylic acid (2), an analogue of the potent antibiotic thienamycin have been developed. The synthetic steps included chain elongations by the methods of Arndt-Eistert and Masamune, diazo group transfers, oxidative removals of N-protecting 2,4-dimethoxybenzyl and p-methoxyphenyl groups, cyclization involving a carbene insertion reaction, and conversion of the ketone moiety of the bicyclic compound (13b) into an enethiol moiety via enolphosphate activation. The target compound, the sodium salt (14c) did not possess any useful biological activity.

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