Skip to main content
SpringerLink
Log in

δ-Santalolanaloga I Synthesen in der Isocamphanreihe, 27. Mitt.

Syntheses in the isocamphane series, XXVII. Analogues of δ-santalol, I

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

Abstract

The synthesis of 4-(3,3-dimethyl-2-exo-norbornyl)-2-methyl-2-buten-1-ol (5), an analogue of δ-santalol (1) has been described. One route to5 starts with isocamphenilanyl propionic acid (8) which can be prepared in 4 steps from isocamphenilanic acid (9). Also 4 steps lead from8 to the target molecule5 with an overall yield of 24%. By a second and more convergent route, starting from the very easily obtainable bicyclic ketone19, the allylic alcohol5 could be obtained again in 4 steps, but this time with an overall yield of 1.3%. A new and easy synthesis of isocamphenilanyl acetic acid (15), a potential starting material to5, has been described, also the preparation of some new isocamphane derivatives.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literatur

  1. Teil der Diplomarbeit vonPüspök G (1980) Universität Wien

  2. Teil der Diplomarbeit vonAngermayer A (1981) Universität Wien

  3. Teil der Diplomarbeit vonSilbernagel E (1983) Universität Wien

  4. Teil der Diplomarbeit vonManz M (1985) Universität Wien

  5. Buchbauer G (1977) Tetrahedron Lett 1977: 7

    Google Scholar 

  6. Buchbauer G, Wiedenhorn M (1980) Monatsh Chem 111: 1299

    Google Scholar 

  7. Buchbauer G (1978) Monatsh Chem 109: 289

    Google Scholar 

  8. Buchbauer G, Wiltschko M (1978) J Soc Cosmet Sci 29: 307

    Google Scholar 

  9. Naipawer RE, Purzycki KL, Shaffer GW, Erickson RE (1981) A structureodor relationship for Sandalwood aroma chemicals. In:Mookherjee BD, Mussinan CJ (eds) Essential oils. Allured Publishing Corp, Wheaton, Illinois, p 105

    Google Scholar 

  10. Buchbauer G, Hell I, Schindler K (1981) Monatsh Chem 112: 841

    Google Scholar 

  11. Brunke EJ, Klein E (1982) Chemistry of Sandalwood fragrance. In:Theimer ET (ed) Fragrance chemistry. The science of smell. Academic Press, New York, p 397

    Google Scholar 

  12. Hana GW, Buchbauer G, Koch H (1976) Monatsh Chem 107: 945

    Google Scholar 

  13. de Tribolet P, Schinz H (1954) Helv Chim Acta 37: 1798

    Google Scholar 

  14. Langlois G (1919) Ann Chim (Paris) [9] 12: 265

    Google Scholar 

  15. Spreitzer H, Schiffer Ch, Buchbauer G (1986)Liebigs Ann Chem 1986:1578

    Google Scholar 

  16. Meins P,Bruns K (1975) Dtsch Offenlegungsschrift 2517620

  17. Strong JG (1971) Dtsch Offenlegungsschrift 2210791

  18. Suga K, Watanabe S (1967) Austr J Chem 20: 2033

    Google Scholar 

  19. Kheifits LA, Il'ina GI, Moldovanskaya GI (1969) Zhurnal Org Khim (Engl Ed) 5: 1590

    Google Scholar 

  20. Lo Cicero JC, Johnson RT (1952) J Am Chem Soc 74: 2094

    Google Scholar 

  21. Buchbauer G, Hana GW, Koch H (1976) Monatsh Chem 107: 387

    Google Scholar 

  22. Evans EA (1956) J Chem Soc 1956: 4691

    Google Scholar 

  23. Kobler H, Schuster KH, Simchen G (1978) Liebigs Ann Chem 1978: 1946

    Google Scholar 

  24. Huisman HO (1975) Synthesis 1975: 626

    Google Scholar 

  25. Staab HA, Bräunling H (1962) Liebigs Ann Chem 654: 119

    Google Scholar 

  26. Buchbauer G (1978) Monatsh Chem 109: 3

    Google Scholar 

  27. Stork G, Kraus GA, Garcia GA (1974) J Org Chem 39: 3459

    Google Scholar 

  28. Buchbauer G, Klissenbauer E (1978) Monatsh Chem 109: 499

    Google Scholar 

  29. Diplomarbeit vonKarner F (1984) Universität Wien

  30. Basu NK, Ghatak UR, Sengupta G, Dutta PC (1965) Tetrahedron 21: 2641

    Google Scholar 

  31. Grundon MF, Henbest HB, Scott MD (1963) J Org Chem 28: 1855

    Google Scholar 

  32. Hutchins RO, Kandasamy D (1975) J Org Chem 40: 2530

    Google Scholar 

  33. Tietze LF, Eicher T (1981) Reaktionen und Synthesen im organischchemischen Praktikum, Thieme, Stuttgart New York, S 36

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Universität Wien, A-1090, Wien, Österreich

    Gerhard Buchbauer, Gabriele Püspök, Adelheid Angermayer, Elisabeth Silbernagel & Marisa Manz

Authors
  1. Gerhard Buchbauer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gabriele Püspök
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Adelheid Angermayer
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Elisabeth Silbernagel
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Marisa Manz
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Auszugsweise vorgetragen auf der gemeinsamen, wissenschaftlichen Tagung der ÖPhG und DPhG am 11. September 1986 in Innsbruck.

26. Mitt:Buchbauer G,Pernold W,Ittner M,Ahmadi MF,Dobner R,Reidinger R (1985) Monatsh Chem 116: 1209

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buchbauer, G., Püspök, G., Angermayer, A. et al. δ-Santalolanaloga I Synthesen in der Isocamphanreihe, 27. Mitt.. Monatsh Chem 118, 387–398 (1987). https://doi.org/10.1007/BF00809950

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00809950

Keywords

Search

Navigation