Ring reversal of a spirocyclic patchouli odorant: Molecular modeling, synthesis, and odor of 6-hydroxy-1,1,6-trimethylspiro[4.5]decan-7-one

European Journal of Organic Chemistry

Volumn , Issue 14, 2007, Pages 2257-2267

  Kraft, Philip ^a   Bruneau, Audrey ^a  

^a GIVAUDAN SCHWEIZ AG   (Switzerland)

Author keywords

Ketohydroxylation; Olfactory properties; Patchouli; Spiro compounds; Structure activity relationships

Indexed keywords

EID: 34250635144     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600815     Document Type: Article

References (55)

1. a) I. Calvino, "II nome, il naso" in Sotto il sole giaguaro, Opere di Italo Calvino, Oscar Mondadori, Milano, 2002, p. 7;
2. b) English ed: I. Calvino, "The Name, the Nose" in Under the Jaguar Sun, A Harvest Book, Harcourt Brace & Company, San Diego, CA, 1988, p. 69;
3. c) German ed.: I. Calvino, "Der Name, die Nase" in Unter der Jaguar-Sonne - Drei Erzählungen, Carl Hanser Verlag, München, 1987, pp. 9-10.
4. P. Kraft, C. Weymuth, C. Nussbaumer, Eur. J. Org. Chem. 2006, 1403-1412.
5. P. Kraft, W. Eichenberger, D. Frech, Eur. J. Org. Chem. 2005, 3233-3245.
6. a) W. Oppolzer, V. Snieckus, Angew. Chem. 1978, 90, 506-516;
7. Angew. Chem. Int. Ed. Engl. 1978, 17, 476-504;
8. b) D. F. Taber, Intramolecular Diels-Alder and Alder Ene Reactions, Reactivity and Structure Concepts in Organic Chemistry Vol. 18, Springer-Verlag, Berlin, 1984, pp. 61-93.
9. S. Antoniotti, E. Duñach, Synthesis 2003, 2753-2762.
10. a) W. Oppolzer, Angew. Chem. 1989, 101, 39-53;
11. Angew. Chem. Int. Ed. Engl. 1989, 28, 38-60;
12. b) W. Oppolzer, Pure Appl. Chem. 1990, 62, 1941-1948;
13. c) W. Oppolzer in Comprehensive Organic Synthesis (Ed.: B. M. Trost), Pergamon Press, Oxford 1991, Vol. 5, pp. 29-61.
14. G. Stork, R. L. Danheiser, J. Org. Chem. 1973, 38, 1775-1776.
15. J.-C. Jung, R. Kache, K. K. Vines, Y.-S. Zheng, P. Bijoy, M. Valluri, M. A. Avery, J. Org. Chem. 2004, 69, 9269-9284.
16. P. J. Kocienski, G. Cernigliaro, G. Feldstein, J. Org. Chem. 1977, 42, 353-355.
17. M. C. Pirrung, J. Am. Chem. Soc. 1981, 103, 82-87.
18. a) G. Dauphin, J.-C. Gourcy, H. Veschambre, Tetrahedron: Asymmetry 1992, 3, 595-598;
19. b) B. Delpech, D. Calvo, R. Lett, Tetrahedron Lett. 1996, 37, 1015-1018.
20. a) H. Lehmkuhl, Bull. Soc. Chim. Fr. 1981, 87-95;
21. b) W. Oppolzer, P. Schneider, Helv. Chim. Acta 1986, 69, 1817-1820.
22. a) W. Oppolzer, F. Schröder, S. Kahl, Helv. Chim. Acta 1997, 80, 2047-2057;
23. b) W. Oppolzer, F. Flachsmann, Helv. Chim. Acta 2001, 84, 416-430.
24. a) R. Appel, Angew. Chem. 1975, 87, 863-874;
25. Angew. Chem. Int. Ed. Engl. 1975, 14, 801-821;
26. b) A. K. Bose, B. Lal, Tetrahedron Lett. 1973, 14, 3937-3940.
27. M. Labrouillère, C. Le Roux, H. Gaspard-Iloughmane, J. Dubac, Synlett 1994, 723-724.
28. V. K. Yadav, K. G. Babu, Tetrahedron 2003, 59, 9111-9116.
29. E. J. Corey, C. U. Kim, M. Takeda, Tetrahedron Lett. 1972, 13, 4339-4342.
30. B. Neiss, W. Steglich, Angew. Chem. 1978, 90, 556-557;
31. Angew. Chem. Int. Ed. Engl. 1978, 17, 522-523.
32. a) S. A. Godleski, R. S. Valpey, J. Org. Chem. 1982, 47, 383-384;
33. b) J.-E. Bäckvall, J.-O. Vågberg, K. L. Granberg, Tetrahedron Lett. 1989, 30, 617-620.
34. M. T. Reetz, W. F. Maier, I. Chatziiosifidis, A. Giannis, H. Heimbach, U. Löwe, Chem. Ber. 1980, 113, 3741-3757.
35. A. Giannis, Diplomarbeit, Rheinische Friedrich-Wilhelms-Universität Bonn, 1980, p. 49.
36. K. Narasaka, T. Sakakura, T. Uchimaru, D. Guédin-Vuong, J. Am. Chem. Soc. 1984, 106, 2954-2961.
37. a) I. M. Downie, J. B. Holmes, J. B. Lee, Chem. Ind. 1966, 900-901;
38. b) P. Kraft, K. Popaj, Eur. J. Org. Chem. 2004, 4995-5002.
39. a) T. Cohen, T. Tsuji, J. Org. Chem. 1961, 26, 1681;
40. b) T. M. Santosusso, D. Swern, J. Org. Chem. 1975, 40, 2764-2769.
41. J. A. Ramírez, E. G. Gros, L. R. Galagovsky, Tetrahedron 2000, 56, 6171-6180.
42. Y. Q. Tu, S. K. Ren, Y. X. Jia, B. M. Wang, A. S. C. Chan, M. C. K. Choi, Tetrahedron Lett. 2001, 42, 2141-2144.
43. H. Hioki, H. Ooi, M. Hamano, Y. Mimura, S. Yoshio, M. Kodama, S. Ohta, M. Yanai, S. Ikegami, Tetrahedron 2001, 57, 1235-1246.
44. V. VanRheenen, R. C. Kelly, D. J. Cha, Tetrahedron Lett. 1976, 17, 1973-1976.
45. a) B. Plietker, J. Org. Chem. 2003, 68, 7123-7125;
46. b) B. Plietker, Org. Lett. 2004, 6, 289-291;
47. c) B. Plietker, J. Org. Chem. 2004, 69, 8287-8296;
48. d) B. Plietker, Tetrahedron: Asymmetry 2005, 16, 3453-3459;
49. e) B. Plietker, Eur. J. Org. Chem. 2005, 1919-1929.
50. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936-3938.
51. R. F. Brown, N. M. van Gulick, J. Am. Chem. Soc. 1955, 77, 1089-1092.
52. a) P. Weyerstahl, J. Prakt. Chem. 1994, 336, 95-109;
53. b) B. D. Mookherjee, K. K. Light, I. D. Hill in 178th ACS National Meeting, Washington D. C., Sept. 9-14, 1979, Abstracts of papers, I, AGFD 55;
54. B. D. Mookherjee, K. K. Light, I. D. Hill in Essential Oils (Eds.: B. D. Mookherjee, C. J. Mussinan), Allured Publishing Corp., Wheaton, IL, 1981, pp. 246-272.
55. R. Becker, K. Jansen, F. G. M. Vogel, Perfum. Flavor. 1990, 15 (Nov./Dec), 29-33.