Synthesis of new exo- and endo-3,8-dihydro-β-santalols and other norbornyl-derived alcohols

Chemistry and Biodiversity

Volumn 7, Issue 3, 2010, Pages 623-638

  Muratore, Agnès ^a,b   Clinet, Jean Claude ^a   Duñach, Elisabet ^b  

^a Laboratoire de Recherche   (France)

^b UNIVERSITÉ DE NICE SOPHIA ANTIPOLIS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BETA SANTALOL; FRAGRANCE; NORBORNANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; HYDROGENATION; SMELLING; SYNTHESIS;

ALCOHOLS; SANTALUM; SESQUITERPENES; SMELL; STEREOISOMERISM;

SANTALUM;

EID: 77949719139     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200900119     Document Type: Article

References (32)

1. E. J. Brunke, E. Klein, in 'Fragrance Chemistry: The science of the sense of smell', Academic Press, NY, 1982; E. J. Brunke, K. G. Fahlbusch, G. Schmaus, J. Vollhardt, in 'The Chemistry of Sandalwood Odour - A Review of the Last 10 Years', Proceedings 15èmes Journées Int. Huiles Essentielles, Dignes-les-Bains, France, Sept. 5-7, 1996.
2. F. W. Semmler, Chem. Ber. 1908, 41, 1488.
3. F. W. Semmler, Chem. Ber. 1910, 43, 1893.
4. E.-J. Brunke, F.-J. Hammerschmidt, H. Struwe, Tetrahedron Lett. 1980, 21, 2405.
5. R. L. Snowden, P. Sonnay, G. Ohloff, Helv. Chim. Acta 1981, 64, 25.
6. E. J. Corey, H. Yamamoto, J. Am. Chem. Soc. 1970, 92, 226.
7. H. Baumann, W. Hoffmann, Liebigs Ann. Chem. 1979, 743.
8. R. G. Lewis, D. H. Gustafon, W. F. Erman, Tetrahedron Lett. 1967, 8, 401.
9. E. J. Corey, H. A. Kirst, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1970, 92, 6314.
10. A. Krotz, G. Helmchen, Tetrahedron: Asymmetry 1990, 1, 537.
11. E.-J. Brunke, Dragoco-Report 1981, 28, 251.
12. W. F. Erman, T. J. Flautt, J. Org. Chem. 1962, 27, 1526.
13. B. Auger, E. Giraudi, WO 9222518, 1993; T. Markert, K. Bruns, V. Porrmann, D. Merkel, DE 4124886, 1993; J. B. Hall, W. J. Wiegers, US 4104203, 1978; G. Buchbauer, F. Zechmeister-Machhart, P. Weiss-Greilar, P. Wolschann, Arch. Pharm. 1997, 330, 112.
14. R. Eilerman, P. Christenson, J. Yurecko, T. Zebovitz, US 4891447, 1990.
15. B. Hölscher, N. A. Braun, B. Weber, C.-H. Kappey, M. Meier, W. Pickenhagen, Helv. Chim. Acta 2004, 87, 1666;
16. G. Buchbauer, I. Stappen, C. Pretterklieber, P. Wolschann, Eur. J. Med. Chem. 2004, 39, 1039.
17. G. Buchbauer, P. Lebada, H. Spreitzer, P. Wolschann, Liebigs Ann. 1995, 9, 1693.
18. M. Gautschi, J. A. Bajgrowicz, P. Kraft, Chimia 2001, 55, 379.
19. W. I. Fanta, W. F. Erman, J. Org. Chem. 1972, 37, 1624.
20. a) C. Chapuis, Chem. Biodiversity 2004, 1, 980;
21. b) J. A. Bajgrowicz, G. Frater, Enantiomer 2000, 5, 225.
22. I. Stappen, J. Höfinghoff, S. Friedl, C. Pammer, P. Wolschann, G. Buchbauer, Eur. J. Med. Chem. 2008, 43, 1525.
23. A. Nikiforov, L. Jirovetz, G. Buchbauer, V. Raverdino, Spectrosc. Int. J. 1988, 6, 283.
24. J. Mane, J.-J. Chanot, F. Le Borgne, M. Schroeder, FR 2831165, 2001.
25. A. Muratore, E. Duñach, J.-C. Clinet, C. Plessis, Chem. Biodiversity 2008, 5, 1099.
26. H. O. House, R. S. Ro, J. Am. Chem. Soc. 1958, 80, 2428.
27. W. R. Vaughan, S. R. Perry Jr., J. Am. Chem. Soc. 1952, 74, 5355;
28. S. Beckmann, H. Geiger, Chem. Ber. 1959, 92, 2411;
29. K. Alder, R. Hartmann, W. Roth, Chem. Ber. 1960, 93, 2271;
30. Z. Zhu, J. H. Espenson, J. Am. Chem. Soc. 1997, 119, 3507.
31. E.-i. Negishi, A. O. King, J. M. Tour, Org. Synth. 1990, Coll. Vol. 7, 63;
32. E.-i. Negishi, A. O. King, W. L. Klima, W. Patterson, A. Silveira Jr., J. Org. Chem. 1980, 45, 2526.