Abstract
An efficient synthesis of 3-(E)-hydroxy- and 3-(E)-acetoxypropenylcephem derivatives, key intermediates for the synthesis of 3-(E)-propenylcephalosporins was achievedvia Stille coupling reaction of 3-trifloxycephem with 3-(E)-tributylstannylallylic alcohol.
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References Cited
Beeby, P. J. and Edwards, J. A., 3-(3-Substituted prop-1-enyl)cephalosporins.J. Med. Chem., 20, 1665 (1977).
Farina, V., Baker, S. R. and Hauck, S. I., Palladium catalysis in cephalosporin chemistry: General methodology for the synthesis of cephem side chains.J. Org. Chem., 54, 4962 (1989).
Hanaki, H., Akagi, H., Nomura, S., Unemi, N. and Hiramatsu, K., Structure-activity relationships of cephalosporin derivatives against methicillin-resistantStaphylococcus aureus andEnterococcus faecalis.J. Antibiotics, 49, 402 (1996).
Iimura, S., Imae, K., Hasegawa, T., Okita, T., Tamaoka, M., Murata, S., Kamachi, H. and Kamei, H., Cephalosporins having a heterocylclic catechol in the C3 side chain, II. Improvement of pharmacokinetic profile.J. Antibiotics, 46, 850 (1993).
Jung, M. E. and Light, L. A., Preparation of iodoallylic alcohols via hydrostannylation: Spectroscopic proof of structures.Tetrahedron Lett., 23, 3851 (1982).
Kamachi, H., Okita, T., Hoshi, H., Okuyama, S. and Naito, T., Synthesis of geometrical isomers of 3-(3-acetoxy and 3-carbamoyl-1-propenyl)cephalosporins and their structure-activity relationship.J. Antibiotics, 45, 998 (1992).
Kant, J. A., Synthetic approach to 3-substituted cephalosporins: Carbon-carbon bond formation at C-3 of the cephem via organocuprate chemistry.J. Org. Chem., 58, 2296 (1993).
Lee, J. Y., Lee, Y. S., Suk, D. W., Woo, E.-R., Chung, B. Y. and Park, H., Synthesis and biological activity of quaternary ammoniopropenylcephalosporins with hydroxylated alicyclic or aliphatic amines.J. Antibiotics, 49, 1286 (1996).
Lee, Y. S., Lee, Y. S. and Park, H., Synthesis and biological activities of C-3 heterocyclylcarbon-substituted novel cephalosporins.J. Antibiotics, 49, 405 (1996).
Walker, D. G., Brodfuehrer, P. R., Shih, K. M. and Sapino, Jr., C., Use of bistrimethylsilylated intermediate in the preparation of semisynthetic 7-amino-3-substituted-cephems. Expedient synthesis of a new 3-[(1-methyl-1-pyrrolidino)methyl]cephalosporin.J. Org. Chem., 53, 983 (1988).
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Lee, Y.S., Lee, J.Y., Jeong, JH. et al. An efficient synthesis of 3-(E)-hydroxypropenyl cephem derivatives, key intermediates for 3-(E)-ammoniopropenylcephalosporin antibiotics. Arch. Pharm. Res. 20, 288–290 (1997). https://doi.org/10.1007/BF02976160
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DOI: https://doi.org/10.1007/BF02976160