DOI QR코드

DOI QR Code

Novel Synthesis of C-3 Vinylic Cephem Systems

  • Published : 1989.08.20

Abstract

The 3-formyl-2-cephem 4, available from 7-aminocephalosporanic acid has been converted to C-3 vinylic cephems. The reactions involved are the Grignard addition to 4, the conversion of the resulting alcohols to mesylates, and the elimination of the mesyl group by LiCl. When ethylmagnesium iodide is used, only 3-[(E)-1-propenyl] cephem is obtained, which is not easily available by conventional Wittig reaction.

Keywords

References

  1. J. Antibiotics v.38 no.12 H. Yamanaka;T. Chiba;K. Kawabata;H. Takasugi;T. Masugi;T. Takaya
  2. USP 4,423,213 Fujisawa Pharmaceutical Company
  3. J. Antibiotics v.40 no.7 T. Naito;H. Hoshi;S. Aburaki;Y. Abe;J. Okumura;K. Tomatsu;H. Kawaguchi
  4. USP 4,619,925 Bristol-Myers Company
  5. Recent Advances in the Chemistry of ${\beta}$-Lactam Antibiotics A. H. Shingler;N. G. Weir;J. Elks(ed.)
  6. Helv. Chim. Acta. v.58 H. Peter;B. Mueller;H. Bickel
  7. Bull. Korean Chem. Soc. v.9 W. J. Kim;K.-Y. Ko;S.-U. Paik;H. Kim
  8. J. Org. Chem. v.36 E. W. Collington;A. I. Meyers
  9. Heterocycles v.24 D. O. Spry;A. R. Bhala
  10. J. Org. Chem. v.43 W. C. Still;M. Kahn;A. Mitra

Cited by

  1. ChemInform Abstract: Novel Synthesis of C‐3 Vinylic Cephem Systems. vol.21, pp.18, 1989, https://doi.org/10.1002/chin.199018296