Woody pretzels: Spirocycles from vetiver to patchouli and georgywood®

Chemistry and Biodiversity

Volumn 5, Issue 6, 2008, Pages 970-999

  Kraft, Philip ^a  

^a GIVAUDAN SCHWEIZ AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CARBENE; CARBON; CARBONYL DERIVATIVE; FRAGRANCE; KETONE DERIVATIVE; GEORGYONE; NAPHTHALENE DERIVATIVE; PATCHOULI ALCOHOL; PERFUME; SESQUITERPENE; SPIRO COMPOUND;

ALPHA HELIX; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; NONHUMAN; ODOR; REVIEW; SMELLING; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; VETIVERIA; WOODY PLANT; CHEMISTRY; CONFORMATION;

POGOSTEMON CABLIN;

MODELS, MOLECULAR; MOLECULAR CONFORMATION; NAPHTHALENES; ODORS; PERFUME; SESQUITERPENES; SPIRO COMPOUNDS; VETIVERIA;

EID: 52649145391     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200890108     Document Type: Review

References (64)

1. A. Birkin, B. Eichinger, T. Tykwer, 'Perfume - The Story of a Murderer', screenplay from the novel by P. Süskind, Constantin Film Productions GmbH/Film & Entertainment VIP Medienfond 4 GmbH & Co. KG/NEF Productions S. A./Castelao Productions S. A., 2006;
2. 'Das Parfüm - Das Buch zum Film', Diogenes Verlag AG, Zürich, 2006, p. 46.
3. J. E. Amoore, Proc. Sci. Sect. Toilet Goods Assoc. 1962, 37(Suppl.), 1-12, 13-23;
4. J. E. Amoore, Nature (London) 1963, 198, 271;
5. J. E. Amoore, Perf. Essentl. Oil. Res. 1952, 43, 321-323, 330;
6. J. E. Amoore, D. Venstrom, J. Food Sci. 1966, 31, 118.
7. L. Ruzicka, Chem.-Ztg. 1920, 44, 93.
8. L. Doszczak, P. Kraft, H.-P. Weber, R. Bertermann, A. Triller, H. Hatt, R. Tacke, Angew. Chem. 2007, 119, 3431;
9. Angew. Chem., Int. Ed. 2007, 46, 3367.
10. B. Maurer, Seifen, Öle, Fette, Wachse 1980, 106, 347.
11. P. Weyerstahl, H. Marshall, U. Splittgerber, D. Wolf, H. Surburg, Flavour Fragrance J. 2000, 15, 395.
12. D. Kastner, Riechst. Aromen Kosmet. 1977, 27, 79.
13. B. D. Mookherjee, R. W. Trenkle, R. A. Wilson, Indian Perfum. 1992, 36, 313.
14. H. Spreitzer, I. Piringer, W. Holzer, M. Widhalm, Helv. Chim. Acta 1998, 81, 2292.
15. J. A. Marshall, P. C. Johnson, J. Am. Chem. Soc. 1967, 89, 2750;
16. J. A. Marshall, P. C. Johnson, J. Org. Chem. 1970, 35, 192.
17. G. Büchi, D. Berthet, R. Decorzant, A. Gieder, A. Hauser, J. Org. Chem. 1976, 41, 3208.
18. G. H. Büchi, Perfum. Flavor. 1978, 3(2), 1.
19. D. P. Anonis, Perfum. Flavor. 2006, 31(11), 36;
20. D. P. Anonis, Perfum. Flavor. 2007, 32(9), 30.
21. P. Kraft, R. Cadalbert, Synthesis 2002, 2243.
22. P. Weyerstahl, H. Marshall, U. Splittgerber, D. Wolf, Flavour Fragrance J. 2000, 15, 61.
23. P. Kraft, W. Eichenberger, D. Frech, Eur. J. Org. Chem. 2005, 3233.
24. Y. Yamamoto, D. Matsumi, K. Itoh, Chem. Commun. 1998, 875;
25. Y. Yamamoto, D. Matsumi, R. Hattori, K. Itoh, J. Org. Chem. 1999, 64, 3224.
26. P. Teisseire, P. Maupetit, B. Corbier, P. Rouillier, Recherches (Paris) 1974, 19, 36;
27. W. E. Oberhänsli, P. Schönholzer, Recherches (Paris) 1974, 19, 62.
28. B. D. Moohkerjee, 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.
29. J. Gadamer, T. Amenomiya, Arch. Pharm. 1903, 241, 22.
30. W. Treibs, Liebigs Ann. Chem. 1949, 564, 141.
31. F. Näf, R. Decorzant, W. Giersch, G. Ohloff, Helv. Chim. Acta 1981, 64, 1387.
32. K. Yamada, Y. Kyotani, S. Manabe, M. Suzuki, Tetrahedron 1979, 35, 293.
33. J. C. Anderson, S. C. Smith, Synlett 1990, 107.
34. E. Wenkert, D. A. Berges, N. F. Golob, J. Am. Chem. Soc. 1978, 100, 1263;
35. E. Wenkert, T. S. Arrhenius, J. Am. Chem. Soc. 1983, 105, 2030.
36. V. van Rheenen, J. Chem. Soc. C 1969, 314.
37. P. Kraft, C. Weymuth, C. Nussbaumer, Eur. J. Org. Chem. 2006, 1403.
38. M. Nishizawa, H. Yamada, Y. Hayashi, J. Org. Chem. 1987, 52, 4878.
39. D. Schummer, G. Höfle, Synlett 1990, 705.
40. G. Köbrich, Angew. Chem. 1973, 85, 494;
41. Angew. Chem., Int. Ed. 1973, 12, 464.
42. P. Kraft, A. Bruneau, Eur. J. Org. Chem. 2007, 2257.
43. B. Plietker, J. Org. Chem. 2003, 68, 7123;
44. B. Plietker, Org. Lett. 2004, 6, 289;
45. B. Plietker, J. Org. Chem. 2004, 69, 8287;
46. B. Plietker, Tetrahedron: Asymmetry 2005, 16, 3453;
47. B. Plietker, Eur. J. Org. Chem. 2005, 1919.
48. M. T. Reetz, W. F. Maier, I. Chatziiosifidis, A. Giannis, H. Heimbach, U. Löwe, Chem. Ber. 1980, 113, 3741.
49. W. Renold, R. Näf-Müller, U. Keller, B. Willhalm, G. Ohloff, Helv. Chim. Acta 1974, 57, 1301;
50. R. Kaiser, A. Kappeler, D. Lamparsky, Helv. Chim. Acta 1978, 61, 387.
51. P. Kraft, K. Popaj, A. Abate, Synthesis 2005, 2798.
52. A. Goeke, to Givaudan, PCT Int. Appl. WO 2004/000776 A1 (Chem. Abstr. 2004, 140, 59802);
53. A. Goeke, D. Mertl, G. Brunner, Angew. Chem. 2005, 117, 101;
54. Angew. Chem., Int. Ed. 2005, 44, 99.
55. A. P. S. Narula, in 'Perspectives in Flavor and Fragrance Research', Eds. P. Kraft, K. A. D. Swift, Verlag Helvetica Chimica Acta, Zurich, 2005, p. 163; A. P. S. Narula, Chem. Biodivers. 2004, 1, 1992.
56. C. Nussbaumer, G. Fráter, P. Kraft, Helv. Chim. Acta 1999, 82, 1016.
57. M. Erman, M. Williams, P. Whelan, C. Cardenas, M. Antipin, Perfum. Flavor. 2001, 26 (2), 16;
58. M. B. Erman, H. M. Hoffmann, C. G. Cardenas, to Millennium Specialty Chemicals, Eur. Pat. Appl. EP O 985 651 A1 (Chem. Abstr. 2000, 132, 207981).
59. P. Kraft, Synthesis 1999, 695;
60. P. Kraft, S. Gallo, Synthesis 2004, 381.
61. P. Kraft, D. Frech, U. Müller, G. Fráter, Synthesis 2006, 2215.
62. S. Hong, E. J. Corey, J. Am. Chem. Soc. 2006, 128, 1346.
63. P. Kraft, K. Popaj, Eur. J. Org. Chem. 2008, 261.
64. T. Hudlicky, J.W. Reed, 'The Way of Synthesis - Evolution of Design and Methods for Natural Products', Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007, p. 35 (patchouli), p. 229 (cedarwood), and p. 255 (vetiver).