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Vol. 25 No. 11 (2013): Vol 25 Issue 11

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An Efficient Synthesis of Dichotomine A via Cyclization of L-Tryptophan Derivative

https://doi.org/10.14233/ajchem.2013.14662
Xiu Xiao Shi
School of Pharmacy, Lanzhou University, Lanzhou 730000, P.R. China
Dian He
School of Pharmacy, Lanzhou University, Lanzhou 730000, P.R. China
Shao Bai Li
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P.R. China
Xin Lei
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P.R. China
Huan Yang
School of Pharmacy, Lanzhou University, Lanzhou 730000, P.R. China

Corresponding Author(s) : Dian He

hed@lzu.edu.cn

Asian Journal of Chemistry, Vol. 25 No. 11 (2013): Vol 25 Issue 11

Abstract

A new synthetic method for dichotomine A is reported. The key step of the synthetic process is the efficient cyclization of L-tryptophan derivative via a modified Bischler-Napieralski reaction which aluminium chloride is used as a mild catalyst. Dichotomine A is obtained in 5 steps and 63.9 % yield.

Keywords

Dichotomine A Aluminium chloride β-Carboline alkaloids Cyclization
Xiao Shi, X., He, D., Bai Li, S., Lei, X., & Yang, H. (2013). An Efficient Synthesis of Dichotomine A via Cyclization of L-Tryptophan Derivative. Asian Journal of Chemistry, 25(11), 6387–6390. https://doi.org/10.14233/ajchem.2013.14662
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References
  1. A. Bolognese, G. Correale, M. Manfra, A. Lavecchia, O. Mazzoni, E. Novellino, P. La Colla, G. Sanna and R. Loddo, J. Med. Chem., 47, 849 (2004).
  2. M.A. Lynch, O. Duval,A. Sukhanova, J. Devy, S.P. Mackay, R.D. Waigh and I. Nabiev, Bioorg. Med. Chem. Lett., 11, 2643 (2001).
  3. J. Ishida, H.-K. Wang, K.F. Bastow, C.-Q. Hu and K.-H. Lee, Bioorg. Med. Chem. Lett., 9, 3319 (1999).
  4. J. Ishida, H.K. Wang, M. Oyama, M.L. Cosentino, Q.H. Chang and K.H. Lee, J. Nat. Prod., 64, 958 (2001).
  5. M. Laronze, M. Boisbrun, S. Leonce, B. Pfeiffer, P. Renard, O. Lozach, L. Meijer, A. Lansiaux, C. Bailly, J. Sapi and J.-Y. Laronze, Bioorg. Med. Chem., 13, 2263 (2005).
  6. A.M. Sobhani and S.A. Ebrahimi, J. Pharm. Sci., 5, 19 (2002).
  7. B. Sun, T. Morikawa, H. Matsuda, S. Tewtrakul, L.J. Wu, S. Harima and M. Yoshikawa, J. Nat. Prod., 67, 1464 (2004).
  8. N. Sotomayor, E. Dominguez and E. Lete, J. Org. Chem., 61, 4062 (1996).
  9. R.S. Kusurkar, S.K. Goswami and S.M. Vyas, Tetrahedron Lett., 44, 4761 (2003).
  10. (a) J.P. Wolfe, in ed.: J.J. Li, Name Reactions in Heterocyclic Chemistry, John Wiley & Sons, p. 376 (2005); (b) D.D. Holsworth, in ed.: J.J. Li, Name Reactions in Heterocyclic Chemistry, John Wiley & Sons, p. 465 (2005).
  11. M. Agnusdei, M. Bandini, A. Melloni and A. Umani-Ronchi, J. Org. Chem., 68, 7126 (2003).
  12. H. Zhang and R.C. Larock, Org. Lett., 3, 3083 (2001).
  13. N. Kanekiyo, T. Kuwada, C. Tominari and S. Hibino, J. Org. Chem., 66, 8793 (2001).
  14. K. Omura, T. Choshi, S. Watanabe, Y. Satoh, J. Nobuhiro and S. Hibino, Chem. Pharm. Bull., 56, 237 (2008).
  15. I. Nemet and L. Varga-Defterdarovic, Bioorg. Med. Chem., 16, 4551 (2008).
  16. Q. Zhang, J. Dong, X.-X. Shi and X. Lu, Eur. J. Org. Chem., 17, 3317 (2012).
  17. D. Robaa, C. Enzensperger, A.S. Eldin, M.M. Hefnawy, H.I. El-Subbagh, T.A. Wani and J. Lehmann, J. Med. Chem., 54, 7422 (2011).
  18. J. Cobo, M. Nogueras, J.N. Low and R. Rodríguez, Tetrahedron Lett., 49, 7271 (2008).
  19. E. Awuah and A. Capretta, J. Org. Chem., 75, 5627 (2010).
  20. G. Bringmann, T. Gulder, B. Hertlein, Y. Hemberger and F. Meyer, J. Am. Chem. Soc., 132, 1151 (2010).
  21. (a) D. Vaccari, P. Davoli, C. Ori, A. Spaggiari and F. Prati, Synlett., 2807 (2008); (b) A. Spaggiari, P. Davoli, L.C. Blaszczak and F. Prati, Synlett., 661 (2005).
  22. R.Z. Fu, X.X. Xu, Q. Dang and X. Bai, J. Org. Chem., 70, 10810 (2005).
  23. R.H. Manske, Chem. Rev., 30, 145 (1942).
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