Skip to main content
Log in

Synthese und Geruch von (E)- und (Z)-bis-homo-ß-Santalol

Synthesis and odour of (E)- and (Z)-bis-homo-ß-santalol

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

The synthesis of the title compounds is described. Guided by theoretical considerations and molecular modeling studies, the influence of the bulky group opposite to the osmophorically important primary hydroxyl function on the odour impression is determined. The organoleptic evaluation proved the predicted sandal like odour of the (Z)-isomer and its also predicted absence with (E)-isomer. A moderate increase of the volume of the bulky group shows no influence on the sandalwood odour of the new analogue.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literatur

  1. Haunschmidt C (1985) Diplomarbeit, Universität Wien

  2. Tröscher F (1988) Diplomarbeit, Universität Wien

  3. Spreitzer H, Rösslhuber I, Kienzl H, Dörrer E, Buchbauer G (1990) Monatsh Chem121: 195

    Google Scholar 

  4. Spreitzer H, Laszloffy B, Lebada Ph, Buchbauer G (1991) Liebigs Ann Chem 391

  5. Buchbauer G, Leonhardsberger K, Winiwarter S, Wolschann P (1992) Helv Chim Acta75: 174

    Google Scholar 

  6. Buchbauer G, Lebada Ph, Spreitzer H, Wolschann P (1995) Liebigs Ann Chem 1693

  7. Buchbauer G, Spreitzer H, Öckher B, Pretterklieber C, Piringer I, Wolschann P (1995) Monatsh Chem126: 467

    Google Scholar 

  8. Buchbauer G, Hillisch A, Mraz K, Wolschann P (1994) Helv Chim Acta77: 2286

    Google Scholar 

  9. Buchbauer G, Spreitzer H, Zechmeister-Machhart F, Pleßl M (1989) Monatsh Chem120: 299

    Google Scholar 

  10. Julia M, Julia S, Guégan R (1960) Bull Soc Chim Fr 1072

  11. Buchbauer G (1978) Monatsh Chem109: 289

    Google Scholar 

  12. Corey EJ, Hartmann R, Vatakencherry PA (1962) J Am Chem Soc84: 2611

    Google Scholar 

  13. Braband J, Mühlstädt M, Mann G (1970) Tetrahedron26: 3667

    Google Scholar 

  14. Umbreit M, Sharpless K (1977) J Am Chem Soc99: 5526

    Google Scholar 

  15. Krotz A, Helmchen G (1990) Tetrahedron Asymmetry1: 537

    Google Scholar 

  16. Still WC, Gennari C (1983) Tetrahedron Lett24: 4405

    Google Scholar 

  17. Liotta CL, Harris HP, Cook FL (1974) J Org Chem39: 2445

    Google Scholar 

  18. Takai K, Hotta Y, Oshima K, Nozaki H (1980) Bull Chem Soc Jpn53: 1698

    Google Scholar 

  19. Brunke E-J (1983) Dragoco Reports30: 27

    Google Scholar 

  20. Spreitzer H, Buchbauer G (1984) Helv Chim Acta67: 1112

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buchbauer, G., Spreitzer, H., Zechmeister-Machhart, F. et al. Synthese und Geruch von (E)- und (Z)-bis-homo-ß-Santalol. Monatsh Chem 127, 747–753 (1996). https://doi.org/10.1007/BF00817266

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00817266

Keywords

Navigation