Natural Product Structure Elucidation: 1950 → 2000

  • Carl Djerassi


Until the early 1960s, some of the greatest organic chemists of this century honed and displayed their chemical skills by elucidating the structures of increasingly complicated natural products of the <1000 Dalton molecular range. Chemical knowledge, intuition, and laboratory skill were responsible for the solution of these problems. But as the number and power of new physical methods increased, structure elucidation has turned from chemistry into applied spectroscopy and computer-driven X-ray crystallography. What are the costs and rewards associated with these methodological changes and what intellectual and practical motivation now inspires modern natural product chemists?


Natural Product Structure Elucidation Absolute Configuration Macrolide Antibiotic English School 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    C. Djerassi, Steroids Made It Possible, American Chemical Society, Washington, DC, 1990.Google Scholar
  2. 2.
    C. Djerassi, The Pill, Pigmy Chimps, and Degas’ Horse, Basic Books, New York, 1992.Google Scholar
  3. 3.
    C. Djerassi, Pure & Appl. Chem., 41, 113 (1975).CrossRefGoogle Scholar
  4. 4.
    Ref.1, pp. 116-128.Google Scholar
  5. 5.
    L. Ruzicka, Experientia 9, 357 (1953).CrossRefGoogle Scholar
  6. 6.
    C. Djerassi, W. Rittel, A. L. Nussbaum, F. W. Donovan, J. Herran, J. Am. Chem. Soc., 76, 6410 (1954).CrossRefGoogle Scholar
  7. C. Djerassi, W. Rittel, J. Am. Chem. Soc., 79, 3528 (1957).CrossRefGoogle Scholar
  8. 7.
    C. Djerassi, S. Burstein, J. Am. Chem. Soc., 80, 2593 (1958).CrossRefGoogle Scholar
  9. 8.
    C. Djerassi, J. A. Zderic, J. Am. Chem. Soc., 78, 2907, 6390 (1956).CrossRefGoogle Scholar
  10. 9.
    S. Masamune, C. U. Kim, K. E. Wilson, G. O. Spessard, P. E. Georghiou, G. S. Bates, J. Am. Chem. Soc., 97, 3512 (1975).CrossRefGoogle Scholar
  11. 10.
    H. Leuchs, Ber., 41, 1711 (1908).Google Scholar
  12. H. Leuchs, M. Mengelberg, Chem. Ben. 82, 250 (1949).Google Scholar
  13. 11.
    R. Robinson, Proc. Roy. Soc. London 130A, 431 (1931).Google Scholar
  14. 12.
    R. B. Woodward, W. J. Brehm, A. L. Nelson, J. Am. Chem. Soc., 69, 2250 (1947) — a preliminary communication recording the final structure of strychnine as determined by Robinson and by Woodward.CrossRefGoogle Scholar
  15. 13.
    R. B. Woodward, Experientia, Suppl. II (14th Int. Congr. Pure & Appl. Chem.), 213 (1955).Google Scholar
  16. 14.
    F. Kröhnke, Chem. Ber., 85 (11) LV (1952).CrossRefGoogle Scholar
  17. 15.
    C. Djerassi, D. H. Smith, C. W. Crandell, N. A. B. Gray, J. G. Nourse, M. R. Lindley, Pure & Appl. Chem., 54, 2425 (1982).CrossRefGoogle Scholar
  18. 16.
    J. G. Nourse, D. H. Smith, R. E. Carhart, C. Djerassi, J. Am. Chem. Soc., 102, 6289 (1980).CrossRefGoogle Scholar
  19. 17.
    C. Djerassi, D. H. Smith, T. H. Varkony, Naturwiss., 66, 9 (1979).CrossRefGoogle Scholar
  20. 18.
    A. R. Battersby, Science, 264, 1551 (1994).CrossRefGoogle Scholar
  21. 19.
    E. M. Gordon, R. W. Barrett, W. J. Dower, S. P. A. Fodor, M. A. Gallop, J. Med. Chem., 37, 1385 (1994).CrossRefGoogle Scholar
  22. 20.
    R. McDaniel, S. Ebert-Khosla, D. A. Hopwood, C. Khosla, Science, 262, 1546 (1993).CrossRefGoogle Scholar
  23. 21.
    C. Kao, L. Katz, C. Khosla, Science, 265, 509 (1994).CrossRefGoogle Scholar
  24. 22.
    K. S. Jayaraman, Nature, 370, 587 (1994).Google Scholar
  25. 23.
    C. Djerassi, Science, 258, 203 (1992).CrossRefGoogle Scholar
  26. 24.
    B. W. Bower, J. C. Avise, Science, 266, 713 (1994).Google Scholar
  27. 25.
    D. M. Putterman, Nature, 371, 553 (1994).CrossRefGoogle Scholar
  28. 26.
    L. S. Gold, T. H. Slone, B. R. Stern, N. B. Manley, B. N. Ames, Science, 258, 261 (1992).CrossRefGoogle Scholar
  29. 27.
    B. Witkop, Med. Res. Rev., 12(3), 195 (1992).CrossRefGoogle Scholar
  30. 28.
    Y. Y. Lin, M. Risk, S. M. Ray, D. Van Engen, J. Clardy, J. Golik, J. C. James, K. Nakanishi, J. Am. Chem. Soc., 103, 6773 (1981).CrossRefGoogle Scholar
  31. 29.
    M. S. Lee, D. J. Repeta, K. Nakanishi, M. G. Zagorski, J. Am. Chem. Soc., 108, 7855 (1986).CrossRefGoogle Scholar
  32. 30.
    K. C. Nicolaou, E. A. Theodorakis, F. P. J. T. Rutjes, J. Tiebes, M. Sato, E. Untersteller and X.-Y. Xiao, J. Am. Chem. Soc., 117, 1171 (1995).CrossRefGoogle Scholar
  33. K. C. Nicolaou, F. P. J. T. Rutjes, E. A. Theodorakis, J. Tiebes, M. Sato, E. Untersteller, J. Am. Chem. Soc., 117, 1173 (1995).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1997

Authors and Affiliations

  • Carl Djerassi
    • 1
  1. 1.Department of ChemistryStanford UniversityStanfordUSA

Personalised recommendations