Download PDF
Synthesis 2009(15): 2501-2504  
DOI: 10.1055/s-0029-1217393
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile and Efficient Total Synthesis of Taspine

Bin Chenga, Sanqi Zhanga, Liyong Zhub, Jie Zhanga, Qiang Lia, Ailin Shana, Langchong He*a
a Research & Engineering Center for Natural Medicine, School of Medicine, Xi’an Jiaotong University, Xi’an 710061, P. R. of China
Fax: +86(29)82655451; e-Mail: helc@mail.xjtu.edu.cn;
b College of Chemistry & Materials Science, Shannxi Normal University, Xi’an 710062, P. R. of China
Further Information

Publication History

Received 27 February 2009
Publication Date:
08 June 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

The facile and efficient total synthesis of taspine was achieved in 10 steps in high yield (16.5% overall) from commercially available isovanillin. Key steps in the synthesis are preparation of a symmetrical homodimer employing a classical Ullmann coupling reaction, and introduction of an allyl substituent by the Claisen rearrangement reaction. Significantly, the facile synthetic scheme proposed in this work has the characteristics of mild reaction conditions, inexpensive reagents, higher yield, and simple operation.

Key words

taspine - natural product - total synthesis - Ullmann coupling - Claisen rearrangement

    References

  • 1 Li Y. Yang G. He L. Zhong Yao Cai  2007,  30:  220 ; Chem. Abstr. 2008, 149, 87126
    Google Scholar
  • 2 Perdue GP. Blomster RN. Blake DA. Farnsworth NR. J. Pharm. Sci.  1979,  68:  124 
    Google Scholar
  • 3a Dong Y. He L. Chen F. Zhongguo Yao Xue Za Zhi  2005,  140:  826 ; Chem. Abstr. 2006, 145, 465570
    Google Scholar
  • 3b Pieters L. de Bruyne T. Van Poel B. Vingerhoets R. Totte J. Vanden Berghe D. Vlietinck A. Phytomedicine  1995,  2:  17 
    Google Scholar
  • 3c Porras-Reyes BH. Lewis WH. Roman J. Simchowitz L. Mustoe TA. Proc. Soc. Exp. Biol. Med.  1993,  203:  18 
    Google Scholar
  • 4a Zhang Y. He L. Zhong Yao Cai  2007,  30:  429 ; Chem. Abstr. 2008, 149, 548368
    Google Scholar
  • 4b Zhang Y. He L. Zhou Y. Phytomedicine  2008,  15:  112 
    Google Scholar
  • 4c Zhang Y. He L. Wang H. Zhongguo Zhong Yao Za Zhi  2007,  32:  953 ; Chem. Abstr. 2008, 148, 345994
    Google Scholar
  • 4d Itokawa H. Ichihara Y. Mochizuki M. Enomori T. Morita H. Shirota O. Inamatsu M. Takeya K. Chem. Pharm. Bull.  1991,  39:  1041 
    Google Scholar
  • 5 Tsacheva I. Rostan J. Iossifova T. Vogler B. Odjakova M. Navas H. Kostova I. Kojouharova M. Kraus W. Z. Naturforsch. C, J. Biosci.  2004,  59:  528 
    Google Scholar
  • 6 Rollinger JM. Schuster D. Baier E. Ellmerer EP. Langer T. Stuppner H. J. Nat. Prod.  2006,  69:  1341 
    CrossrefGoogle Scholar
  • 7a Zhang Y. He L. Meng L. Luo W. Xu X. Cancer Lett.  2008,  262:  103 
    Google Scholar
  • 7b Zhang Y. He L. Meng L. Luo W. Vascul. Pharmacol.  2008,  48:  129 
    Google Scholar
  • 8 Kelly TR. Xie RL. J. Org. Chem.  1998,  63:  8045 
    CrossrefGoogle Scholar
  • 9 Trost BM. Tang W. Toste FD. J. Am. Chem. Soc.  2005,  127:  14785 
    CrossrefGoogle Scholar
  • 10 Bermejo A. Andreu I. Suvire F. Leonce S. Caignard DH. Renard P. Pierre A. Enriz RD. Cortes D. Cabedo N. J. Med. Chem.  2002,  45:  5058 
    CrossrefGoogle Scholar
  • 11 Fang F. Aiguo J. Zhongguo Yi Yao Gong Ye Za Zhi  2006,  37:  80 
    Google Scholar
  • 12 Quideau S. Pouységu L. Oxoby M. Looney MA. Tetrahedron  2001,  57:  319 
    CrossrefGoogle Scholar
  • 13 Montoya-Pelaez PJ. Uh Y.-S. Lata C. Thompson MP. Lemieux RP. Crudden CM. J. Org. Chem.  2006,  71:  5921 
    CrossrefGoogle Scholar
  • 14 Khanbabaee K. Großer M. Tetrahedron  2002,   58:  1159 
    Google Scholar
  • 15 Baret P. Bkguin C. Gaude D. Gellon G. Mourral C. Pierre J.-L. Serratrice G. Favier A. Tetrahedron  1994,   50:  2077 
    Google Scholar
  • 16 Scarpati ML. Bianco A. Scalzo RL. Synth. Commun.  1991,  33:  849 
    Google Scholar
  • 17 Bishop JE. Mathis CA. Gerdes JM. Whitney JM. Eaton AM. Mailman RB. J. Med. Chem.  1991,  34:  1612 
    CrossrefGoogle Scholar
  • 18 Clive DLJ. Yu M. Sannigrahi M. J. Org. Chem.  2004,  69:  4116 
    CrossrefGoogle Scholar