Advertisement

Monatshefte für Chemie / Chemical Monthly

, Volume 111, Issue 6, pp 1299–1306 | Cite as

Zur Synthese von β-Isosantalol

Synthesen in der Isocamphanreihe, 14. Mitt.
  • Gerhard Buchbauer
  • Manfred Wiedenhorn
Organische Chemie und Biochemie

Syntheses in the isocamphane series, XIV. The synthesis of β-isosantalol

Abstract

The synthesis of a new allylic alcohol with a norbornane skeleton is described. The convergent synthesis leads from 3-methylene-norbornan-2-one to β-isosantalol (6). An important structural parameter of6 is derived from β-Santalol (1), the main constituent of east indian sandalwoodoil with a powerful woody fragrance. Another structural parameter of6 is derived from isosantalol (3) with a weak woody odour. The odour of the new alcohol6 is weaker than that of3, probably because of too much osmophoric groups and a very reactivecis-1,3-butadiene-system. Another possible route to6 by means of aWittig-reaction did not succed.

Keywords

C−C-Bond formation 3-Methylenenorbornan-2-one Osmophoric group Riley oxidation Santalolanalogue Woody odour 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literatur

  1. 3.
    W. I. Fanta undW. F. Erman, J. Org. Chem.37, 1624 (1972).Google Scholar
  2. 4.
    G. Buchbauer, Tetrahedron Lett.1977, 7.Google Scholar
  3. 5.
    G. Buchbauer, Mh. Chem.109, 289 (1978).Google Scholar
  4. 6.
    G. Buchbauer, Arzneim.-Forsch.29, 1500 (1979).Google Scholar
  5. 7.
    H. Krieger, A. Arstila undH. Malo, Finn. Chem. Lett.1978, 156;H. Krieger, K. Manninen undJ. Paasivirta, Suom. Kemistil.B39, 8 (1966);H. Krieger, Suom. KemistilB35, 10, 71 (1962).Google Scholar
  6. 8.
    M. Julia, S. Julia undR. Guegan, Bull. Soc. Chim. Fr.1960, 1072.Google Scholar
  7. 9.
    W. R. Vaughan undD. M. Teegarden, J. Amer. Chem. Soc.96, 4902 (1974).Google Scholar
  8. 10.
    M. Baumann undW. Hoffmann, Ann. Chem.1979, 743.Google Scholar
  9. 11.
    G. Buchbauer, M. A. März undE. Ehrmann-Falkenau, Sci. Pharm.47, 319 (1979).Google Scholar
  10. 12.
    W. C. Still, M. Kahn undA. Mitra, J. Org. Chem.43, 2923 (1978).Google Scholar
  11. 13.
    O. Motl, V. Herout undF. Sorm, Coll. Czechosl. Chem. Commun.23, 1293 und 1297 (1958).Google Scholar
  12. 14.
    U. T. Bhalerao undH. Rapoport, J. Amer. Chem. Soc.93, 4835 (1971).Google Scholar
  13. 15.
    R. Greenwald, M. Chaykovsky undE. J. Corey, J. Org. Chem.28, 1128 (1963).Google Scholar
  14. 16.
    J. M. Conia undJ. C. Limasset, Bull. Soc. Chim. Fr.1967, 1936.Google Scholar
  15. 17.
    U. Huber, Diplomarbeit, Universität Wien, 1980.Google Scholar
  16. 18.
    F. J. Gottschalk undP. Weyerstahl, Chem. Ber.113, 555 (1980).Google Scholar
  17. 19.
    H. C. Kretschmar undW. F. Erman, U.S. Patent 3 673 261 (1972).Google Scholar
  18. 20.
    W. Sturm, in: Geruch- und Geschmackstoffe (F. Drawert, Hrsg.), S. 265. Nürnberg: Hans Carl. 1975.Google Scholar
  19. 21.
    M. G. J. Beets, Amer. Perfum.76 (6), 54 und76 (10), 12 (1961);M. G. J. Beets, Parfum. Cosmet. Savons5, 167 (1962).Google Scholar
  20. 22.
    W. Steiner, Parf. u. Kosmetik50, 41 (1969).Google Scholar

Copyright information

© Springer-Verlag 1980

Authors and Affiliations

  • Gerhard Buchbauer
    • 1
  • Manfred Wiedenhorn
    • 1
  1. 1.Institut für Pharmazeutische ChemieUniversität WienWienÖsterreich

Personalised recommendations