A Facile Synthesis of Symmetrical Dimeric Steroid-pyrazines

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

Zenon Łotowski, Agnieszka Gryszkiewicz, Jolanta B. Borowiecka, Agnieszka Nikitiuk and Jacek W. Morzycki


Abstract

The reaction of steroidal 2α-bromo-3-ketones (e.g. 2α-bromocholestan-3-one 2) with ammonia followed by hydrolysis and air-oxidation affords the easily separable mixture of the trans and cis dimeric steroid-pyrazines (3 and 4, respectively).


References

  1. G. R. Pettit, M. Inoue, Y. Kamano, D. L. Herald, C. Arm, C. Dufresne, N. D. Christie, J. M. Schmidt, D. L. Doubek and T. S. Krupa, J. Am. Chem. Soc., 1988, 110, 2006 CrossRef CAS.
  2. S. Fukuzawa, S. Matsunaga and N. Fusetani, Tetrahedron, 1995, 51, 6707 CrossRef CAS.
  3. These series of compounds are among the most potent cytostatics ever screened by the National Cancer Institute (USA). For a short review see: A. Ganesan, Stud. Nat. Prod. Chem., 1996, 18, 875 Search PubMed.
  4. T. G. LaCour, C. Guo, S. Bhandaru, M. R. Boyd and P. L. Fuchs, J. Am. Chem. Soc., 1998, 120, 692 CrossRef CAS.
  5. C. Guo, S. Bhandaru and P. L. Fuchs, J. Am. Chem. Soc., 1996, 118, 10672 CrossRef CAS.
  6. M. Drögemuller, T. Flessner, R. Jautelat, U. Scholzf and E. Winterfeldt, Eur. J. Org. Chem., 1998, 2811 CrossRef.
  7. Y. Pan, R. L. Merriman, L. R. Tanzer and P. L. Fuchs, Bioorg. Med. Chem. Lett., 1992, 2, 967 CrossRef CAS.
  8. C. H. Heathcock and S. C. Smith, J. Org. Chem., 1994, 59, 6828 CrossRef CAS.
  9. H. E. Smith and A. A. Hicks, J. Org. Chem., 1971, 36, 3659 CrossRef CAS.
  10. A. Kramer, U. Ullmann and E. Winterfeldt, J. Chem. Soc., Perkin Trans. 1, 1993, 2865 RSC.
  11. J. W. Morzycki, A. Gryszkiewicz, Z. Lotowski and W. J. Szczepek, Collect. Czech. Chem. Commun., 1998, 63, 1589 CrossRef CAS.