Musk or violet? Design, synthesis and odor of seco-derivates of a musky carotol lead

Tetrahedron

Volumn 62, Issue 52, 2006, Pages 12211-12219

  Kraft, Philip ^a   Popaj, Kasim ^a  

^a GIVAUDAN SCHWEIZ AG   (Switzerland)

Author keywords

Alkynols; Carotol; Chemoselective hydrogenation; Ionone odorants; Odor structure correlation; seco Derivatives

Indexed keywords

ACETALDEHYDE; BROMINE DERIVATIVE; LEAD; MAGNESIUM CHLORIDE; MUSK; PYRIDINIUM DERIVATIVE;

ARTICLE; GRIGNARD REACTION; ODOR; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 33750941618     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.10.020     Document Type: Article

References (29)

1. Kulesza J., Kula J., and Kwiatkowski W. Riechstoffe, Aromen, Koerperpflegemittel 23 (1973) 34-37
2. Kraft P. In: Rowe D.J. (Ed). Chemistry and Technology of Flavors and Fragrances (2005), Blackwell, CRC, Oxford, Boca Raton 162-165
3. Kula J., Bonikowski R., Staniszewska M., Krakowiak A., Wieczorek M.W., Majzner W.R., and Bujacz G.D. Eur. J. Org. Chem. (2002) 1826-1829
4. Sestanj K. Croat. Chem. Acta 43 (1962) 211-217
5. Kraft P. In: Swift K.A.D. (Ed). Advances in Flavours and Fragrances: From the Sensation to the Synthesis (2002), The Royal Society of Chemistry, Cambridge 138-146
6. Saucy G., Marbet R., Lindlar H., and Isler O. Chimia 12 (1958) 326-327
7. Saucy G., Marbet R., Lindlar H., and Isler O. Helv. Chim. Acta 42 (1959) 1945-1955
8. Lee K., and Wiemer D.F. J. Org. Chem. 56 (1991) 5556-5560
9. Chanley J.D., and Sobotka H. J. Am. Chem. Soc. 71 (1949) 4140-4141
10. Bates E.B., Jones E.R.H., and Whiting M.C. J. Chem. Soc. (1954) 1854-1860
11. Corey E.J., Katzenellenbogen J.A., and Posner G.H. J. Am. Chem. Soc. 89 (1967) 4245-4247
12. Borden W.T. J. Am. Chem. Soc. 92 (1970) 4898-4901
13. Grant B., and Djerassi C. J. Org. Chem. 39 (1974) 968-970
14. Thies R.W., and Daruwala K.P. J. Org. Chem. 52 (1987) 3798-3806
15. Kraft P., Popaj K., and Abate A. Synthesis (2005) 2798-2809
16. Cahiez G., and Laboue B. Tetrahedron Lett. 33 (1992) 4439-4442
17. Cahiez G., and Laboue B. Tetrahedron 45 (1989) 4163-4176
18. Imamoto T., Takiyama N., Nakamura K., Hatajima T., and Kamiya Y. J. Am. Chem. Soc. 111 (1989) 4392-4398
19. Dimitrov V., Bratovanov S., Simova S., and Kostova K. Tetrahedron Lett. 35 (1994) 6713-6716
20. Conlon D.A., Kumke D., Moeder C., Hardiman M., Huston G., and Sailer L. Adv. Synth. Catal. 346 (2004) 1307-1315
21. Martin J.C., and Arhart R.J. J. Am. Chem. Soc. 93 (1971) 2339-2342
22. Martin J.C., and Arhart R.J. J. Am. Chem. Soc. 93 (1971) 4327-4329
23. Tse B., and Kishi Y. J. Org. Chem. 59 (1994) 7807-7814
24. Ball S., Goodwin T.W., and Morton R.A. Biochem. J. 42 (1948) 516-523
25. Baskaran S., Islam I., Raghavan M., and Chandrasekaran S. Chem. Lett. (1987) 1175-1178
26. Kraft P., Eichenberger W., and Frech D. Eur. J. Org. Chem. (2005) 3233-3245
27. Surburg H., and Panten J. Common Fragrance and Flavor Materials: Preparation, Properties and Uses. 5th compl. rev. ed. (2006), Wiley-VCH, Weinheim p 92
28. Brenna E., Fuganti C., Serra S., and Kraft P. Eur. J. Org. Chem. (2002) 967-978
29. Brenna E., Delmonte M., Fuganti C., and Serra S. Helv. Chim. Acta 84 (2001) 69-86