Download PDF
Synthesis 2010(5): 807-810  
DOI: 10.1055/s-0029-1218603
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereospecific Total Synthesis of (+)-Davana Acid, (+)-Nordavanone and (+)-Davanone

Gowravaram Sabitha*, M. Nagendra Prasad, M. Bhikshapathi, J. S. Yadav
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com;
Further Information

Publication History

Received 4 November 2009
Publication Date:
11 December 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

A short, total synthesis of (+)-davana acid, (+)-nordavanone and (+)-davanone, which are principle components of davana oil, is described. The notable features are the use of the Evans syn aldol reaction and cyclic ether formation by an intramolecular SN2 displacement reaction as key steps.

Key words

Evans aldol - cyclic ether - (-)-linalool - natural product - davana oil

    References

  • 1a Misra LN. Chandra A. Thaken RS. Phytochemistry  1991,  30:  549 
    Google Scholar
  • 1b Thomas AF. Ozainne M. Helv. Chim. Acta  1974,  57:  2062 
    Google Scholar
  • 1c Sipma G. van der Wal B. Recl. Trav. Chim. Pays-Bas  1968,  87:  715 
    Google Scholar
  • 2 Hethelye E. Tetenyi P. Kettenes van der Bosh J. Salemink C. Heerma W. Verluis C. Kloosterman J. Sipma G. Phytochemistry  1981,  20:  1847 
    CrossrefGoogle Scholar
  • 3 Thomas AF. Thommen W. Willhalm B. Hagaman EW. Wenkert E. Helv. Chim. Acta  1974,  57:  2055 
    CrossrefGoogle Scholar
  • 4 Husain A. Virmani OP. Sharma A. Kumar A. Misra LN. Major Essential Oil-Bearing Plants in India   CIMAP; Lucknow: 1988.  p.167-181  
    Google Scholar
  • 5a Thomas AF. Pitton G. Helv. Chim. Acta  1971,  1890 
    Google Scholar
  • 5b Baslas RK. Flavour Ind.  1971,  2:  370 
    Google Scholar
  • 6 Vajs V. Trifunovic S. Janackovic P. Sokovic M. Milosavljevic S. Tesevic V. J. Serb. Chem. Soc.  2004,  69:  969 
    CrossrefGoogle Scholar
  • 7 Perfumi M. Paparelli F. Cingolani M. J. Essent. Oil Res.  1995,  7:  387 
    CrossrefGoogle Scholar
  • 8a Molander GA. Hass J. Tetrahedron  1999,  55:  617 
    Google Scholar
  • 8b Birch AJ. Corrie JET. Rao GSRS. Aust. J. Chem.  1970,  23:  1811 
    Google Scholar
  • 8c Naegeli P. Weber G. Tetrahedron Lett.  1970,  959 
    Google Scholar
  • 9a Honda Y. Ori A. Tsuchihashi G.-I. Chem. Lett.  1987,  1259 
    Google Scholar
  • 9b Bartlett PA. Holmes CP. Tetrahedron Lett.  1983,  24:  1365 
    Google Scholar
  • 10 Morrison KC. Litz JP. Scherpelz KP. Dossa D. Vosburg DA. Org. Lett.  2009,  11:  2217 
    CrossrefGoogle Scholar
  • 11 Sharpless KB. Amberg W. Bennani YL. Crispino GA. Hartung J. Jeong K.-S. Kwong H.-L. Morikawa K. Wang Z.-M. Xu D.-Q. Zhang X.-L. J. Org. Chem.  1992,  57:  2768 
    Google Scholar
  • 12 Evans DA. Bartoli J. Shih TL. J. Am. Chem. Soc.  1981,  103:  2127 
    CrossrefGoogle Scholar
  • 13 Hong B.-C. Hong J.-H. Tsai Y.-C. Angew. Chem. Int. Ed.  1998,  4:  37 
    Google Scholar