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Synlett 2008(14): 2209-2212  
DOI: 10.1055/s-2008-1078255
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

The Enantioselective Total Synthesis and Unambiguous Proof of the Absolute Stereochemistry of Pervilleine C

Ketav Kulkarnia, Anne Y. Zhaob, Anthony W. Purcellb, Patrick Perlmutter*a
a School of Chemistry, Monash University, PO Box 23, Victoria, 3800, Australia
Fax: +61(3)99054597; e-Mail: Patrick.perlmutter@sci.monash.edu.au;
b Department of Biochemistry and Molecular Biology, The Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, 3010 Victoria, Australia
Further Information

Publication History

Received 30 May 2008
Publication Date:
13 August 2008 (online)

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Abstract

The first enantioselective, total synthesis of the naturally occurring, potent cancer MDR reversal agent pervilleine C is reported. Each enantiomer of the natural product has been prepared as well as the enantiomers of the corresponding 8-oxa-pervilleine C.

Key words

pervilleines - MDR reversal - total synthesis - [4+3] cycloadditions - enantioselective oxidative hydroboration

    References

  • 1a Silva G. Cui B. Chavez D. You M. Chai H. Rasoanaivo P. Lynn S. O’Neill M. Lewis J. Besterman J. Monks A. Farnsworth N. Cordell G. Pezzuto J. Kinghorn A. J. Nat. Prod.  2001,  64:  1514 
    Google Scholar
  • 1b Mi Q. Cui B. Lantvit D. Reyes-Lim E. Chai H. Pezzuto J. Kinghorn D. Swanson S. Anticancer Res.  2003,  23:  3607 
    Google Scholar
  • 1c Mi Q. Cui B. Silvia GL. Lantvit D. Lim E. Chai H. Hollingshead MG. Mayo JG. Kinghorn AD. Pezzuto JM. Cancer Lett.  2002,  184:  13 
    Google Scholar
  • 1d Mi Q. Cui B. Silvia GL. Lantvit D. Lim E. Chai H. You M. Hollingshead MG. Mayo JG. Kinghorn AD. Pezzuto JM. Cancer Res.  2001,  61:  4030 
    Google Scholar
  • 2a Hoffmann HMR. Kim H. Eur. J. Org. Chem.  2000,  2195 
    Google Scholar
  • 2b Hoffmann HMR. Angew. Chem., Int. Ed. Engl.  1973,  12:  819 
    Google Scholar
  • 2c Hoffmann HMR. Angew. Chem.  1984,  23:  1 
    Google Scholar
  • 2d Hoffmann HMR. Iqbal MN. Tetrahedron Lett.  1975,  50:  4487 
    Google Scholar
  • 3a Noyori R. Hayakawa Y. Org. React.  1983,  29:  163 
    Google Scholar
  • 3b Hayakawa Y. Baba Y. Makino S. Noyori R. J. Am. Chem. Soc.  1978,  100:  1786 
    Google Scholar
  • 3c Noyori R. Makino S. Okita T. Hayakawa Y. J. Org. Chem.  1975,  40:  806 
    Google Scholar
  • 3d Takay H. Hayakawa Y. Makino S. Noyori R. J. Am. Chem. Soc.  1978,  100:  1778 
    Google Scholar
  • 4a Mann J. Tetrahedron  1986,  42:  4611 
    Google Scholar
  • 4b Mann J. de Almeida Barbosa LC. J. Chem. Soc., Perkin Trans. 1  1992,  787 
    Google Scholar
  • 5a Brown HC. Ayyangar NR. Zweifel G. J. Am. Chem. Soc.  1964,  86:  397 
    Google Scholar
  • 5b Brown HC. Singaram B. J. Org. Chem.  1984,  49:  945 
    Google Scholar
  • 5c Brown HC. Joshi NN. J. Org. Chem.  1988,  53:  4059 
    Google Scholar
  • 5d Lautens M. Ma S. Tetrahedron Lett.  1996,  37:  1727 
    Google Scholar
  • 5e Corey EJ. Snider BB. J. Am. Chem. Soc.  1972,  94:  2549 
    Google Scholar
  • 6 Fung VA. DeGraw JI. Synthesis  1976,  311 
    Article in Thieme ConnectGoogle Scholar
  • 7 Corey EJ. Venkateswarlu A. J. Am. Chem. Soc.  1972,  94:  6190 
    CrossrefGoogle Scholar