Issue 0, 1974
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Electrochemical reduction of cephalosporanic acids

Michihiko Ochiai,   Osami Aki,   Akira Morimoto,   Taiiti Okada,   Kazuo Shinozaki  and  Yutaka Asahi  

Abstract

Electrochemical reduction of cephalosporanic acid derivatives (I) bearing various substituents at the 3-position gave the corresponding 3-methylenecepham derivatives (II), a new class of cephalosporins. Reductive opening of the 3-hydroxymethyl-3-cephem-4-carboxylic acid lactone (IV) was effected to give (II) by cathodic reaction. The 3-methylenecepham derivatives (II) were readily isomerized to the 3-methyl-3-cephem derivatives (III) providing a new synthesis of cephalexin [7-(D-2-amino-2-phenylacetamido)-3-methyl-3-cephem-4-carboxylic acid](IIIc). The reaction mechanism is discussed on the basis of deuteriation and polarography of the cephalosporins involved.

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Article information

DOI
https://doi.org/10.1039/P19740000258
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1974, 258-262

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Electrochemical reduction of cephalosporanic acids

M. Ochiai, O. Aki, A. Morimoto, T. Okada, K. Shinozaki and Y. Asahi, J. Chem. Soc., Perkin Trans. 1, 1974, 258 DOI: 10.1039/P19740000258

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