Synthesis of d,l-Norlabdane Oxide and Related Odorants: An Intramolecular Radical Approach

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4779-4785

  Zoretic, Phillip A ^a   Fang, Haiquan ^a   Ribeiro, Anthony A ^b  

^a EAST CAROLINA UNIVERSITY   (United States)

^b DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001205029     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980211a     Document Type: Article

References (48)

1. Ohloff, G. Fragrance Chemistry. The Science of the Sense of Smell; Theimer, E. T.; Academic Press: New York, 1982; pp 535. Sell, C. Chem. Ind. 1990, 20, 516.
2. Ohloff, G. Fragrance Chemistry. The Science of the Sense of Smell; Theimer, E. T.; Academic Press: New York, 1982; pp 535. Sell, C. Chem. Ind. 1990, 20, 516.
3. (-)-Norlabdane oxide is commonly known under the trade names: Ambrox (Firmenich), Amberlyn (Quest), and Ambroxan (Henkel).
4. Ohloff, G.; Giersch, W.; Pickenhagen, W.; Furrer, A.y; Frei, B. Helv. Chim. Acta 1985, 68, 2022.
5. Stoll, M.; Hinder, M. Helv. Chim. Acta 1950, 33, 1251. Hinder, M.; Stoll, M. Helv. Chim. Acta 1950, 33, 1308.
6. Stoll, M.; Hinder, M. Helv. Chim. Acta 1950, 33, 1251. Hinder, M.; Stoll, M. Helv. Chim. Acta 1950, 33, 1308.
7. (a) Kutney, J. P.; Chen, Y.-H. Can. J. Chem. 1994, 72, 1570.
8. (b) Verstegen-Haaksma, A. A.; Swarts, H. J.; Jansen, B. J. M.; de Groot, A. Tetrahedron 1994, 50, 10095.
9. (c) Barrero, A. F.; Sanchez, J. F.; Alvarez-Manzaneda, E. J.; Altarejos, J.; Munoz, M.; Haidour, A. Tetrahedron 1994, 50, 6653.
10. (d) Gonzalez-Sierra, M.; Ruveda, E. A.; Lopez, J. T.; Cortes, M. J. Heterocycles 1987, 26, 2801.
11. (e) Schenk, H. R.; Gutman, H.; Jeger, O.; Ruzicka, Helv. Chim. Acta 1954, 37, 543.
12. (f) Cambie, R. C.; Joblin, K. N.; Preston, A. F. Aust. J. Chem. 1971, 24, 583.
13. (g) Koyama, H.; Kaku, Y.; Ohno, M. Tetrahedron Lett. 1987, 28, 2863.
14. (h) Nishi, Y.; Ishihara, H. J. Jpn. Oil Chem. Soc. 1989, 38, 276.
15. (i) Urones, J. G.; Basabe, P.; Marcos, I. S.; Gonzalez, J. L.; Jimenez, V.; Sexmero, M. J.; Lithgow, A. M. Tetrahedron 1992, 48, 9991.
16. (j) J. de Pascual-Teresa; Urones, J. G.; Pedrero, A. M.; Barcala, P. B. Tetrahedron Lett. 1985, 26, 5717.
17. (a) Barton, D. H. R.; Parekh, S. I.; Taylor, D. K.; Tse; C.-l. Tetrahedron Lett. 1994, 35, 5801.
18. (b) Barton, D. H. R.; Taylor, D. K.; Tse, C-l. Tetrahedron Lett. 1994, 35, 9505.
19. (c) Martres, P.; Perfetti, P.; Zahra, J. P.; Waegell, B. Tetrahedron Lett. 1994, 35, 97.
20. (d) Martres, P.; Perfetti, P.; Zahra, J. P.; Waegell, B.; Giraudi, E.; Petrzilka, M. Tetrahedron Lett. 1993, 34, 629.
21. (e) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Altarejos, J.; Salido, S. Ramos, J. M. Tetrahedron 1993, 49, 10405.
22. (f) Martres, P.; Perfetti, P.; Zahra, J. P.; Waegell, B. Tetrahedron Lett. 1991, 32, 765.
23. (g) Christenson, P. A. Tetrahedron, 1988, 44, 1925.
24. (h) Coste-Maniere, I. C.; Zahra, J. P.; Waegell, B. Tetrahedron Lett. 1988, 29, 1017.
25. (i) Decorzant, R.; Vial, C.; Naf, F.; Whitesides, G. M. Tetrahedron, 1987, 43, 1871.
26. (a) Barrero, A. F.; Altarejos, J.; Alvarez-Manzaneda, E. J.; Ramos, J. M.; Salido, S. Tetrahedron 1993, 49, 6251.
27. (b) Barrero, A. F.; Altarejos, J.; Alvarez-Manzaneda, E. J.; Ramos, J. M.; Salido, S. Tetrahedron 1993, 49, 9525.
28. Mori, K.; Tamura, H. Liebigs Ann. Chem. 1990, 361.
29. (a) Barrero, A. F.; Altarejos, J.; Alvarez-Manzaneda; Ramos, J. M.; Salido, S. J. Org. Chem. 1996, 61, 2215.
30. (b) Barco, A.; Benetti, S.; Bianchi, A.; Casolari, A.; Guarmeri, M., Pollini, G. P. Tetrahedron 1995, 57, 8333.
31. (c) Buchi, G.; Wuest, H. Helv. Chim. Acta 1989, 72, 996.
32. (d) Snowden, R. L.; Linder, S. M. Tetrahedron Lett. 1991, 32, 4119.
33. (a) Snowden, R. L.; Eichenberger, J. C.; Linder, S. M.; Sonnay, P.; Vial, C.; Schulte-Elite, K. H. J. Org. Chem. 1992, 57, 955.
34. (b) Neumann, S.; Simon, H. Biol Chem. Hoppe Seyler 1986, 367, 723.
35. (c) Tanimoto, H.; Oritani, T. Tetrahedron Asymmetry, 1996, 7, 1695.
36. Barnes, A. G.; Bevan, P. C. Ger. Offen. CODEN: GWXXBX. DE 3439564 Al 850515; Chem. Abstr. 1985, 103, 85328. For the synthesis of ( -)-norlabdane-2β-ol oxide and the 2-oxo derivative from 2-oxomanoyl oxide, see: Cambie, R. C.; Joblin, K. N.; McCallum, N. K. Aust. J. Chem. 1970, 23, 1439.
37. Barnes, A. G.; Bevan, P. C. Ger. Offen. CODEN: GWXXBX. DE 3439564 Al 850515; Chem. Abstr. 1985, 103, 85328. For the synthesis of ( -)-norlabdane-2β-ol oxide and the 2-oxo derivative from 2-oxomanoyl oxide, see: Cambie, R. C.; Joblin, K. N.; McCallum, N. K. Aust. J. Chem. 1970, 23, 1439.
38. Barnes, A. G.; Bevan, P. C. Ger. Offen. CODEN: GWXXBX. DE 3439564 Al 850515; Chem. Abstr. 1985, 103, 85328. For the synthesis of ( -)-norlabdane-2β-ol oxide and the 2-oxo derivative from 2-oxomanoyl oxide, see: Cambie, R. C.; Joblin, K. N.; McCallum, N. K. Aust. J. Chem. 1970, 23, 1439.
39. Marshall, J. A.; Andrews, R. C. J. Org. Chem. 1985, 50, 1602.
40. Corey, E. J.; Kim, C. U.; Takeda, M. Tetrahedron Lett. 1972, 42, 4339.
41. For recent radical reviews, see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 111. (c) Malacria, M. Chem. Rev. 1996, 96, 289. (d) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (e) Melikyan, G. G. Synthesis 1993, 833.
42. For recent radical reviews, see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 111. (c) Malacria, M. Chem. Rev. 1996, 96, 289. (d) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (e) Melikyan, G. G. Synthesis 1993, 833.
43. For recent radical reviews, see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 111. (c) Malacria, M. Chem. Rev. 1996, 96, 289. (d) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (e) Melikyan, G. G. Synthesis 1993, 833.
44. For recent radical reviews, see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 111. (c) Malacria, M. Chem. Rev. 1996, 96, 289. (d) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (e) Melikyan, G. G. Synthesis 1993, 833.
45. For recent radical reviews, see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 111. (c) Malacria, M. Chem. Rev. 1996, 96, 289. (d) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (e) Melikyan, G. G. Synthesis 1993, 833.
46. Dombroski, M. A.; Kates, S. A.; Snider, B. B. J. Am. Chem. Soc. 1990, 112, 2759 and references within.
47. Barton, D. H. R.; Motherwell, W. B.; Stange, A. Synthesis 1991, 743.
48. Kochi, J. K.; Bemis, A.; Jenkins, C. L. J. Am. Chem. Soc. 1968, 90, 4616.