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)

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.

    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 
  • 1b Mi Q. Cui B. Lantvit D. Reyes-Lim E. Chai H. Pezzuto J. Kinghorn D. Swanson S. Anticancer Res.  2003,  23:  3607 
  • 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 
  • 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 
  • 2a Hoffmann HMR. Kim H. Eur. J. Org. Chem.  2000,  2195 
  • 2b Hoffmann HMR. Angew. Chem., Int. Ed. Engl.  1973,  12:  819 
  • 2c Hoffmann HMR. Angew. Chem.  1984,  23: 
  • 2d Hoffmann HMR. Iqbal MN. Tetrahedron Lett.  1975,  50:  4487 
  • 3a Noyori R. Hayakawa Y. Org. React.  1983,  29:  163 
  • 3b Hayakawa Y. Baba Y. Makino S. Noyori R. J. Am. Chem. Soc.  1978,  100:  1786 
  • 3c Noyori R. Makino S. Okita T. Hayakawa Y. J. Org. Chem.  1975,  40:  806 
  • 3d Takay H. Hayakawa Y. Makino S. Noyori R. J. Am. Chem. Soc.  1978,  100:  1778 
  • 4a Mann J. Tetrahedron  1986,  42:  4611 
  • 4b Mann J. de Almeida Barbosa LC. J. Chem. Soc., Perkin Trans. 1  1992,  787 
  • 5a Brown HC. Ayyangar NR. Zweifel G. J. Am. Chem. Soc.  1964,  86:  397 
  • 5b Brown HC. Singaram B. J. Org. Chem.  1984,  49:  945 
  • 5c Brown HC. Joshi NN. J. Org. Chem.  1988,  53:  4059 
  • 5d Lautens M. Ma S. Tetrahedron Lett.  1996,  37:  1727 
  • 5e Corey EJ. Snider BB. J. Am. Chem. Soc.  1972,  94:  2549 
  • 6 Fung VA. DeGraw JI. Synthesis  1976,  311 
  • 7 Corey EJ. Venkateswarlu A. J. Am. Chem. Soc.  1972,  94:  6190