Simple and Condensed β-Lactams. Part 28.1 The Synthesis of C-Methylcarumonams and of a Related Bis(carbamate)

(Note: The full text of this document is currently only available in the PDF Version )

József Fetter, Ferenc Bertha, Károly Lempert, Attila Sápi and Mária Kajtár-Peredy


Abstract

Racemic carumonam analogues 2a–d are synthesised and found to be devoid of any bacterial activity; NaBH4 reduction of 18 affords both epimers of 8c with the (3RS,4RS)-4-[(1RS)] epimer as the main product, and cyclocondensation of phthalimidoacetyl chloride with racemic imine 14 gives rise to the formation of (3RS,4RS)-4-[(1RS)]-15 as a single epimer.


References

  1. Part 27, Le Thanh Giang, J. Fetter, K. Lempert, M. Kajtár-Peredy and A. Gömöry, Tetrahedron, 1996, 52, 10 169 Search PubMed.
  2. M. Sendai, S. Hashiguchi, M. Tomimoto, S. Kishimoto, T. Matsuo, M. Kondo and M. Ochiai, J. Antibiot., 1985, 38, 346 CAS.
  3. J. Fetter, H. Vásárhelyi, M. Kajtár-Peredy, K. Lempert, J. Tamás and G. Czira, Tetrahedron, 1995, 51, 4763 CrossRef CAS.
  4. D. R. Kronenthal, C. Y. Han and M. K. Taylor, J. Org. Chem., 1982, 47, 2765 CrossRef CAS.
  5. C. M. Cimarusti, H. E. Applegate, H. W. Chang, D. M. Floyd, W. H. Koster, W. A. Slusarchyk and M. G. Young, J. Org. Chem., 1982, 47, 179 CrossRef CAS.
  6. Takeda Chemical Industries, Eur. Pat. Appl., EP 93.376, 1983(Chem. Abstr., 1984, 100, P 209.515z) Search PubMed.
  7. A. Kálmán, personal communication.
  8. M. Cerest, H. Felkin and N. Prudent, Tetrahedron Lett., 1968, 2199 CrossRef CAS.
  9. N. T. Anh and O. Eisenstein, Nouv. J. Chim., 1977, 1, 61; N. T. Anh, Top. Curr. Chem., 1980, 88, 145.
Click here to see how this site uses Cookies. View our privacy policy here.