Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Horizons
  • Published:

Synthesis at the molecular frontier

Nature volume 460, pages 197–201 (2009)Cite this article

Driven by remarkable advances in the understanding of structure and reaction mechanisms, organic synthesis will be increasingly directed to producing bioinspired and newly designed molecules.

This is a preview of subscription content, access via your institution

Relevant articles

Open Access articles citing this article.

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

Prices may be subject to local taxes which are calculated during checkout

Figure 1: Structural and functional inspirations from natural products.

I. SPENCE/VISUALS UNLIMITED/GETTY IMAGES; K. LEE

Figure 2: The development of new reactions for step-economical total synthesis.
Figure 3: The use of cascade reactions to rapidly generate complexity and value.
Figure 4: Developing ideal syntheses.
Figure 5: Function-oriented synthesis as applied to bryostatin.

References

  1. Seebach, D. Angew. Chem. Int. Edn 29, 1320–1367 (1990).

    Article  Google Scholar 

  2. Cornforth, J. W. Aust. J. Chem. 46, 157–170 (1993).

    Article  CAS  Google Scholar 

  3. Wender, P. A. & Miller, B. L. in Connectivity Analysis and Multibond-forming Processes in Organic Synthesis: Theory and Applications (ed. Hudlicky, T.) 27–66 (JAI Press, 1993).

    Google Scholar 

  4. Tietze, L. F. Domino Reactions in Organic Synthesis (Wiley-VCH, 2006).

    Book  Google Scholar 

  5. Nicolaou, K. C. Tetrahedron 59, 6683–6738 (2003).

    Article  CAS  Google Scholar 

  6. Wilson, R. M. & Danishefsky, S. J. J. Org. Chem. 71, 8329–8351 (2006).

    Article  CAS  Google Scholar 

  7. Horvath, I. & Anastas, P. T. Chem. Rev. 107, 2169–2173 (2007).

    Article  CAS  Google Scholar 

  8. Corey, E. J., Czakó, B. & Kürti, L. Molecules and Medicine (John Wiley, 2007).

    Google Scholar 

  9. Hudlicky, T. & Reed, J. W. The Way of Synthesis: Evolution of Design and Methods for Natural Products (Wiley-VCH, 2007).

    Google Scholar 

  10. Trost, B. M. Science 254, 1471–1477 (1991).

    Article  CAS  ADS  Google Scholar 

  11. Maimone, T. J. & Baran, P. S. Nature Chem. Biol. 3, 396–407 (2007).

    Article  CAS  Google Scholar 

  12. Koshino, M., Solin, N., Tanaka, T., Isobe, H. & Nakamura, E. Nature Nanotechnol. 3, 595–597 (2008).

    Article  CAS  Google Scholar 

  13. Sudek, S. et al. J. Nat. Prod. 70, 67–74 (2007).

    Article  CAS  Google Scholar 

  14. Wender, P. A. et al. in Drug Discovery Research (ed. Huang, Z.) 127–162 (John Wiley, 2007).

    Google Scholar 

  15. Sun, M.-K. & Alkon, D. L. Eur. J. Pharmacol. 584, 328–337 (2008).

    Article  CAS  Google Scholar 

  16. Kingston, D. G. & Newman, D. J. Curr. Opin. Drug Discov. Dev. 10, 130–144 (2007).

    CAS  Google Scholar 

  17. Newman, D. J. & Cragg, G. M. J. Nat. Prod. 70, 461–477 (2007).

    Article  CAS  Google Scholar 

  18. Wender, P. A., Kee, J. M. & Warrington, J. M. Science 320, 649–652 (2008).

    Article  CAS  ADS  Google Scholar 

  19. Johnson, H. E., Banack, S. A. & Cox, P. A. J. Nat. Prod. 71, 2041–2044 (2008).

    Article  CAS  Google Scholar 

  20. LaVan, D. A. & Cha, J. N. Proc. Natl Acad. Sci. USA 103, 5251–5255 (2006).

    Article  CAS  ADS  Google Scholar 

  21. Hampp, N. Chem. Rev. 100, 1755–1776 (2000).

    Article  CAS  Google Scholar 

  22. Greenbaum, E. et al. Tech. Dig. Int. Electron. Device Meet. 496–498 (2002).

  23. Wender, P. A. et al. Pure Appl. Chem. 74, 25–31 (2002).

    Article  CAS  Google Scholar 

  24. Hinman, A. & Du Bois, J. J. Am. Chem. Soc. 125, 11510–11511 (2003).

    Article  CAS  Google Scholar 

  25. Chen, M. S. & White, M. C. Science 318, 783–787 (2007).

    Article  CAS  ADS  Google Scholar 

  26. Chen, H., Schlecht, S., Semple, T. C. & Hartwig, J. F. Science 287, 1995–1997 (2000).

    Article  CAS  ADS  Google Scholar 

  27. Wender, P. A., Verma, V. A., Paxton, T. J. & Pillow, T. H. Acc. Chem. Res. 41, 40–49 (2008).

    Article  CAS  Google Scholar 

  28. Robinson, R. J. Chem. Soc. 762–768 (1917).

  29. Chanon, M., Barone, R., Baralotto, C., Julliard, M. & Hendrikson, J. B. Synthesis 1998, 1559–1583 (1998).

    Article  Google Scholar 

  30. Wender, P. A. (ed.) Chem. Rev. 96, 1–600 (1996).

    Article  Google Scholar 

  31. Yoder, R. A. & Johnston, J. N. Chem. Rev. 105, 4730–4756 (2005).

    Article  CAS  Google Scholar 

  32. Vilotijevic, I. & Jamison, T. F. Science 317, 1189–1192 (2007).

    Article  CAS  ADS  Google Scholar 

  33. Curran, D. P. & Kuo, S.–C. Tetrahedron 43, 5653–5661 (1987).

    Article  CAS  Google Scholar 

  34. Padwa, A. & Bur, S. K. Tetrahedron 63, 5341–5378 (2007).

    Article  CAS  Google Scholar 

  35. Nicewicz, D. A., Satterfield, A. D., Schmitt, D. C. & Johnson, J. S. J. Am. Chem. Soc. 130, 17281–17283 (2008).

    Article  CAS  Google Scholar 

  36. Reppe, W. et al. Liebigs Ann. Chem. 560, 1–92 (1948).

    Article  CAS  Google Scholar 

  37. Chappell, D. & Russell, A. T. Org. Biomol. Chem. 4, 4409–4430 (2006).

    Article  CAS  Google Scholar 

  38. Das, A. & Khosla, C. Acc. Chem. Res. 42, 631–639 (2009).

    Article  CAS  Google Scholar 

  39. Hale, K. J., Hummersone, M. G., Manaviazar, S. & Frigerio, M. Nat. Prod. Rep. 19, 413–453 (2002).

    Article  CAS  Google Scholar 

  40. Wender, P. A., DeChristopher, B. A. & Schrier, A. J. E. J. Am. Chem. Soc. 130, 6658–6659 (2008).

    Article  CAS  Google Scholar 

  41. Wulff, J. E., Herzon, S. B., Siegrist, R. & Myers, A. G. J. Am. Chem. Soc. 129, 4898–4899 (2007).

    Article  CAS  Google Scholar 

  42. Towle, M. J. et al. Cancer Res. 61, 1013–1021 (2001).

    CAS  Google Scholar 

  43. Szpilman, A. M., Manthorpe, J. M. & Carreira, E. M. Angew. Chem. Int. Edn 47, 4339–4342 (2008).

    Article  CAS  Google Scholar 

  44. Dubikovskaya, E. A. et al. Proc. Natl Acad. Sci. USA 105, 12128–12133 (2008).

    Article  CAS  ADS  Google Scholar 

  45. Krueger, A. T. & Kool, E. T. Chem. Biol. 16, 242–248 (2009).

    Article  CAS  Google Scholar 

  46. Schreiber, S. L. Science 287, 1964–1969 (2000).

    Article  CAS  ADS  Google Scholar 

  47. Thomas, G. L. et al. Angew. Chem. Int. Edn 47, 2808–2812 (2008).

    Article  CAS  Google Scholar 

  48. Corbett, P. T. et al. Chem. Rev. 106, 3652–3711 (2006).

    Article  CAS  Google Scholar 

  49. McNaughton, B. R., Gareiss, P. C. & Miller, B. L. J. Am. Chem. Soc. 129, 11306–11307 (2007).

    Article  CAS  Google Scholar 

  50. Gareiss, P. C. et al. J. Am. Chem. Soc. 130, 16254–16261 (2008).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Paul A. Wender is in the Chemistry Department and, the Department of Chemical and Systems Biology, by courtesy, Stanford University, 333 Campus Drive, Stanford, California 94305-5080, USA. wenderp@stanford.edu,

    Paul A. Wender

  2. Benjamin L. Miller is in the School of Medicine and Dentistry, University of Rochester, 601 Elmwood Avenue, Box 697, Rochester, New York 14642, USA. Benjamin_miller@urmc.rochester.edu,

    Benjamin L. Miller

Authors
  1. Paul A. Wender
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Benjamin L. Miller
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wender, P., Miller, B. Synthesis at the molecular frontier. Nature 460, 197–201 (2009). https://doi.org/10.1038/460197a

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/460197a

This article is cited by

Search

Advanced search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing