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Zur Synthese von β-Isosantalol

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

Synthesen in der Isocamphanreihe, 14. Mitt.

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.

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Literatur

  1. 3

    W. I. Fanta undW. F. Erman, J. Org. Chem.37, 1624 (1972).

  2. 4

    G. Buchbauer, Tetrahedron Lett.1977, 7.

  3. 5

    G. Buchbauer, Mh. Chem.109, 289 (1978).

  4. 6

    G. Buchbauer, Arzneim.-Forsch.29, 1500 (1979).

  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).

  6. 8

    M. Julia, S. Julia undR. Guegan, Bull. Soc. Chim. Fr.1960, 1072.

  7. 9

    W. R. Vaughan undD. M. Teegarden, J. Amer. Chem. Soc.96, 4902 (1974).

  8. 10

    M. Baumann undW. Hoffmann, Ann. Chem.1979, 743.

  9. 11

    G. Buchbauer, M. A. März undE. Ehrmann-Falkenau, Sci. Pharm.47, 319 (1979).

  10. 12

    W. C. Still, M. Kahn undA. Mitra, J. Org. Chem.43, 2923 (1978).

  11. 13

    O. Motl, V. Herout undF. Sorm, Coll. Czechosl. Chem. Commun.23, 1293 und 1297 (1958).

  12. 14

    U. T. Bhalerao undH. Rapoport, J. Amer. Chem. Soc.93, 4835 (1971).

  13. 15

    R. Greenwald, M. Chaykovsky undE. J. Corey, J. Org. Chem.28, 1128 (1963).

  14. 16

    J. M. Conia undJ. C. Limasset, Bull. Soc. Chim. Fr.1967, 1936.

  15. 17

    U. Huber, Diplomarbeit, Universität Wien, 1980.

  16. 18

    F. J. Gottschalk undP. Weyerstahl, Chem. Ber.113, 555 (1980).

  17. 19

    H. C. Kretschmar undW. F. Erman, U.S. Patent 3 673 261 (1972).

  18. 20

    W. Sturm, in: Geruch- und Geschmackstoffe (F. Drawert, Hrsg.), S. 265. Nürnberg: Hans Carl. 1975.

  19. 21

    M. G. J. Beets, Amer. Perfum.76 (6), 54 und76 (10), 12 (1961);M. G. J. Beets, Parfum. Cosmet. Savons5, 167 (1962).

  20. 22

    W. Steiner, Parf. u. Kosmetik50, 41 (1969).

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Additional information

13. Mitt.:G. Buchbauer undM. Kern, Arch. Pharmaz., im Druck.

Teil der Diplomarbeit vonM. Wiedenhorn, Universität Wien, 1980.

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Buchbauer, G., Wiedenhorn, M. Zur Synthese von β-Isosantalol. Monatshefte für Chemie 111, 1299–1306 (1980). https://doi.org/10.1007/BF00903656

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Keywords

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