Synlett 2006(15): 2469-2471  
DOI: 10.1055/s-2006-950437
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Harounoside, A Naturally Occurring Pentalongin Hydroquinone Bisglucoside

Tuyen Nguyen Vana, Sven Claessensa, Pascal Habonimanaa, Kourosch Abbaspour Tehranib, Luc Van Puyveldea, Norbert De Kimpe*a
a Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
b Department of Organic Chemistry, Faculty of Science, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium
Fax: +32(9)2646243; e-Mail: norbert.dekimpe@UGent.be;
Further Information

Publication History

Received 29 June 2006
Publication Date:
08 September 2006 (online)

Abstract

The recently isolated natural product harounoside, ­namely 5,10-dihydroxy-2H-naphtho[2,3-c]pyran-β-d-bisglucopyranoside, was conveniently synthesized for the first time from pentalongin in 84% yield over three steps.

    References

  • 1 Adjanohoun EJ. Ahyi AMR. Dan Dicko L. Daouda H. Delmas M. De Souza S. Garba M. Guinko S. Kayonga A. N’Golo D. Raynal JL. Saandou M. Contribution aux études ethnobotaniques et floristiques au Niger   A. C. C. T.; France: 1985. 
  • 2 Harouna H. Faure R. Elias R. Debrauwer L. Saadou M. Balansard G. Boudon G. Phytochemistry  1995,  39:  1483 
  • 3 Van Puyvelde L. Hakizayezu D. Brioen P. De Kimpe N. De Vroey C. Bogaerts J. Hakizamungu E. ; Paper presented at the International Congress on Natural Products Research, July 31-August 4, Halifax, Nova Scotia: 1994. 
  • 4 De Kimpe N. Van Puyvelde L. Schripsema J. Erkelens C. Verpoorte R. Magn. Reson. Chem.  1993,  31:  329 
  • 5 Hari L. De Buyck LF. De Pooter HL. Phytochemistry  1991,  30:  1726 
  • 6 Kesteleyn B. De Kimpe N. Van Puyvelde L. J. Org. Chem.  1999,  64:  1173 
  • 7 Kesteleyn B. De Kimpe N. Tetrahedron Lett.  2000,  41:  755 
  • 8 Claessens S. Naidoo D. Mulholland D. Verschaeve L. van Staden J. De Kimpe N. Synlett  2006,  621 
  • 9 Kesteleyn B. De Kimpe N. Van Puyvelde L. Synthesis  1999,  1881 
  • 10 Koenigs W. Knorr E. Ber. Dtsch. Chem. Ges.  1901,  34:  957 
  • 11 Jensen KJ. Meldal M. Bock K. J. Chem. Soc., Perkin Trans. 1  1993,  2119 
  • 12 Tietze LF. Fischer R. Guder HJ. Tetrahedron Lett.  1982,  23:  4661 
  • 13 Lindhorst TK. Kotter S. Kubisch J. Krallmann-Wenzel U. Ehlers S. Kren V. Eur. J. Org. Chem.  1998,  1669 
  • 14 Smits E. Engberts JBFN. Kellogg RM. Van Doren HA. J. Chem. Soc., Perkin Trans. 1  1996,  2873 
  • 15 Schmidt RR. Michel J. Angew. Chem., Int. Ed. Engl.  1980,  9:  731 
  • 16 Brown RT. Scheimann F. Stachulski AV. J. Chem. Res., Synop.  1997,  370 
  • 17 Redoulès D. Perié J. Tetrahedron Lett.  1999,  40:  4811 
  • 18 Aly MRE. Castro-Palomino JC. Ibrahim ESI. El-Ashry ESH. Schmidt RR. Eur. J. Org. Chem.  1998,  2305 
  • 19 Johnsson R. Ellervik U. Synlett  2005,  2939 
  • 20 Masquelin T. Hengartner U. Streith J. Synthesis  1995,  780