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.

  • News & Views
  • Published:

Total synthesis

Towards artificial terpene cyclases

The plant-derived sesquiterpene englerin A is a potent inhibitor of several renal cancer cell lines. Two recent total syntheses have utilized cationic gold(I)-complexes to coax readily available open-chain precursors into englerin's challenging oxotricyclic core with enzyme-like precision.

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

Relevant articles

Open Access articles citing this article.

Access options

Buy this article

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

Figure 1: Comparison of the biosynthesis and the total synthesis of englerin A.

References

  1. Breitmaier, E. Terpenes: Flavors, Fragrances, Pharmaca, Pheromones (Wiley-VCH, 2006).

    Book  Google Scholar 

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

    Article  CAS  Google Scholar 

  3. Tietze, L. F., Brasche, G. & Gericke, K. M. Domino Reactions in Organic Synthesis (Wiley-VCH, 2006).

    Book  Google Scholar 

  4. Ratnayake, R., Covell, D., Ransom, T. T., Gustafson, K. R. & Beutler, J. A. Org. Lett. 11, 57–60 (2009).

    Article  CAS  Google Scholar 

  5. Willot, M. et al. Angew. Chem. Int. Ed. 48, 9105–9108 (2009).

    Article  CAS  Google Scholar 

  6. Zhou, Q., Chen, X. & Ma, D. Angew. Chem. Int. Ed. 49, 3513–3516 (2010).

    Article  CAS  Google Scholar 

  7. Molawi, K., Delpont, N. & Echavarren A. M. Angew. Chem. Int. Ed. 49, 3517–3519 (2010).

    Article  CAS  Google Scholar 

  8. Fürstner, A. Chem. Soc. Rev. 38, 3208–3221 (2009).

    Article  Google Scholar 

  9. Jiménez-Nuñez, E., Claverie, C. K., Nieto-Oberhuber C. & Echavarren, A. M. Angew. Chem. Int. Ed. 45, 5452–5455 (2006).

    Article  Google Scholar 

  10. Chen, K. & Baran, P. S. Nature 459, 824–828 (2009).

    Article  CAS  Google Scholar 

  11. Nicolaou, K. C., Kang, Q., Ng, S. Y. & Chen D. Y.-K. J. Am. Chem. Soc. doi:10.1021/ja102927n (2010).

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Willot, M., Christmann, M. Towards artificial terpene cyclases. Nature Chem 2, 519–520 (2010). https://doi.org/10.1038/nchem.715

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1038/nchem.715

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