Display options
Cite
Brown N, Luo D, Decapo JA, et al. New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development. Tetrahedron Lett. 2009;50(51):7113-7115doi: 10.1016/j.tetlet.2009.09.083.
Brown, N., Luo, D., Decapo, J. A., & Buszek, K. R. (2009). New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development. Tetrahedron letters, 50(51), 7113-7115. https://doi.org/10.1016/j.tetlet.2009.09.083
Brown, Neil, et al. "New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development." Tetrahedron letters vol. 50,51 (2009): 7113-7115. doi: https://doi.org/10.1016/j.tetlet.2009.09.083
Brown N, Luo D, Decapo JA, Buszek KR. New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development. Tetrahedron Lett. 2009 Dec 23;50(51):7113-7115. doi: 10.1016/j.tetlet.2009.09.083. PMID: 20877442; PMCID: PMC2945378.
Copy Download .nbib Format: NLM
Share it on

Tetrahedron Lett. 2009 Dec 23;50(51):7113-7115. doi: 10.1016/j.tetlet.2009.09.083.

New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development.

Tetrahedron letters

Neil Brown, Diheng Luo, Joseph A Decapo, Keith R Buszek

Affiliations

  1. Department of Chemistry, University of Missouri-Kansas City, 205 Spencer Chemical Laboratories, 5100 Rockhill Road, Kansas City, MO 64110, USA.

PMID: 20877442 PMCID: PMC2945378 DOI: 10.1016/j.tetlet.2009.09.083

Abstract

We describe herein an efficient new route to the trikentrins and their related structures using a tandem 6,7-indolyne cycloaddition/Negishi cross-coupling reaction starting from a 4,6,7-tribromoindole (obtained in good yield via the Bartoli indole synthesis). The key step of this second generation route to the trikentrins is based on our observation that the 7-bromo substituent appears to undergo selective metal-halogen exchange and elimination to give the 6,7-indolyne, which is trapped in the presence of excess cyclopentadiene. Subsequent Negishi cross-coupling at the 4-bromoindole position with Et(2)Zn gave directly the same intermediate obtained from our previous work. Application of this chemistry to the construction of trikentrin-related libraries using this general cycloaddition/cross-coupling tactic will also be described.

References

  1. Org Lett. 2009 Jan 1;11(1):201-4 - PubMed
  2. J Am Chem Soc. 2004 Feb 11;126(5):1340-1 - PubMed
  3. Org Lett. 2009 Jun 4;11(11):2349-51 - PubMed
  4. J Am Chem Soc. 2007 Mar 21;129(11):3358-66 - PubMed
  5. Org Lett. 2006 Jul 20;8(15):3403-6 - PubMed
  6. Org Lett. 2005 Mar 31;7(7):1215-8 - PubMed
  7. Org Lett. 2007 Oct 11;9(21):4135-7 - PubMed
  8. J Am Chem Soc. 2006 Apr 26;128(16):5360-1 - PubMed
  9. Org Lett. 2004 May 13;6(10):1589-92 - PubMed
  10. Angew Chem Int Ed Engl. 2002 Oct 18;41(20):3910-2 - PubMed
  11. Org Lett. 2009 Feb 19;11(4):1007-10 - PubMed
  12. J Org Chem. 2007 Feb 16;72(4):1405-11 - PubMed
  13. Tetrahedron Lett. 2009 Jan 7;50(1):63-65 - PubMed

Publication Types

Grant support