Efficient macrocyclization by a novel oxy-oxonia-cope reaction: Synthesis and olfactory properties of new macrocyclic musks

Chemistry - A European Journal

Volumn 18, Issue 23, 2012, Pages 7010-7015

  Zou, Yue ^a,b   Mouhib, Halima ^c   Stahl, Wolfgang ^c   Goeke, Andreas ^b   Wang, Quanrui ^a   Kraft, Philip ^d  

^a FUDAN UNIVERSITY   (China)

^b Givaudan Fragrances (Shanghai) Ltd   (China)

^c RWTH AACHEN UNIVERSITY   (Germany)

^d GIVAUDAN SCHWEIZ AG   (Switzerland)

Author keywords

fragrances; ketones; macrocycles; Prins reaction; rearrangement; structure odor relationship

Indexed keywords

MACRO-CYCLIZATION; MACROCYCLES; MACROCYCLICS; OLFACTORY PROPERTIES; OLFACTORY RECEPTORS; PRINS REACTION; REARRANGEMENT; STRUCTURE-ODOR RELATIONSHIP; SYNTHESIZED STRUCTURES;

FRAGRANCES; KETONES; ORGANIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

CYCLOALKANE DERIVATIVE; MACROCYCLIC COMPOUND; MUSCONE; PERFUME;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HALOGENATION; ODOR; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKYLATION; CYCLIZATION; CYCLOPARAFFINS; HALOGENATION; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; PERFUME; SMELL; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861639922     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200882     Document Type: Article

References (46)

1. G. Ohloff, W. Pickenhagen, P. Kraft, Scent and Chemistry-The Molecular World of Odors, Verlag Helvectica Chimica Acta, Zurich, 2011, p. 339-364
2. P. Kraft, in Chemistry and Technology of Flavors and Fragrances (Ed:, D.J. Rowe,), Blackwell, Oxford, 2005, pp. 143-168
3. P. Kraft in, Perspectives in Flavor and Fragrance Research (Eds.:, P. Kraft, K.A.D. Swift,), Verlag Helvectica Chimica Acta, Zurich, 2005, pp. 127-144
4. G. Fráter, J. Bajgrowicz, P. Kraft, Tetrahedron 1998, 54, 7633-7703
5. P. Kraft, C. Denis, J. Bajgrowicz, G. Fráter, Angew. Chem. 2000, 112, 3106-3138
6. Angew. Chem. Int. Ed. 2000, 39, 2980-3010.
7. C. Fehr, J. Galindo, O. Etter, Eur. J. Org. Chem. 2004, 1953-1957.
8. A. S. Williams, Synthesis 1999, 1707-1723.
9. P. Kraft, C. Berthold, Synthesis 2008, 543-550.
10. P. Kraft, W. Eichenberger, Eur. J. Org. Chem. 2004, 354-365.
11. Y. Zou, C. Ding, L. Zhou, Z. Li, Q. Wang, F. Schoenebeck, A. Goeke, Angew. Chem. 2012, 124, 808
12. Angew. Chem. Int. Ed. 2012, 51, 784.
13. M. H. Hopkins, L. E. Overman, J. Am. Chem. Soc. 1987, 109, 4748-4749.
14. L. E. Overman, Acc. Chem. Res. 1992, 25, 352-359
15. L. E. Overman, L. D. Pennington, J. Org. Chem. 2003, 68, 7143-7157.
16. For a general review on Prins-type macrocyclizations, see:, E. A. Crane, K. A. Scheidt, Angew. Chem. 2010, 122, 8494-8505
17. Angew. Chem. Int. Ed. 2010, 49, 8316-8326.
18. J. J. Jaber, K. Mitsui, S. D. Rychnovsky, J. Org. Chem. 2001, 66, 4679-4686
19. S. R. Crosby, J. R. Harding, C. D. King, G. D. Parker, C. L. Willis, Org. Lett. 2002, 4, 577-580
20. J. E. Dalgard, S. D. Rychnovsky, J. Am. Chem. Soc. 2004, 126, 15662-15663
21. R. Jasti, C. D. Anderson, S. D. Rychnovsky, J. Am. Chem. Soc. 2005, 127, 9939-9945
22. C. S. Barry, N. Bushby, J. R. Harding, R. A. Hughes, G. D. Parker, R. Roe, C. L. Willis, Chem. Commun. 2005, 3727-3729
23. R. Jasti, S. D. Rychnovsky, J. Am. Chem. Soc. 2006, 128, 13640-13648
24. P. O. Miranda, M. A. Ramírez, V. S. Martín, J. I. Padrõn, Chem. Eur. J. 2008, 14, 6260-6268
25. J. D. Elsworth, C. L. Willis, Chem. Commun. 2008, 1587-1589.
26. K. H. Schulte-Elte, A. Hauser, G. Ohloff, Helv. Chim. Acta 1979, 62, 2673-2680
27. J. Tsuji, T. Yamada, M. Kaito, T. Mandai, Tetrahedron Lett. 1979, 20, 2257-2260
28. V. Rautenstrauch, R. L. Snowden, S. M. Linder, Helv. Chim. Acta 1990, 73, 896-901
29. V. P. Kamat, H. Hagiwara, T. Suzuki, M. Ando, J. Chem. Soc. Perkin Trans. 1 1998, 2253-2254
30. Y. Tanabe, N. Matsumoto, T. Higashi, T. Misaki, T. Itoh, M. Yamamoto, K. Mitarai, Y. Nishii, Tetrahedron 2002, 58, 8269-8280
31. O. Knopff, J. Kuhne, C. Fehr, Angew. Chem. 2007, 119, 1329-1332
32. Angew. Chem. Int. Ed. 2007, 46, 1307-1310
33. H. Tsuji, K. Yamagata, Y. Itoh, K. Endo, M. Nakamura, E. Nakamura, Angew. Chem. 2007, 119, 8206-8208
34. Angew. Chem. Int. Ed. 2007, 46, 8060-8062.
35. H. Finkelstein, Ber. Dtsch. Chem. Ges. 1910, 43, 1528-1532.
36. G. E. Keck, C. E. Knutson, S. A. Wiles, Org. Lett. 2001, 3, 707-710
37. D. M. Walba, W. N. Thurmes, R. C. Haltiwanger, J. Org. Chem. 1988, 53, 1046-1056.
38. A. N. Chernega, S. G. Davies, C. J. Goodwin, D. Hepworth, W. Kurosawa, P. M. Roberts, J. E. Thomson, Org. Lett. 2009, 11, 3254-3257
39. A. Abiko, O. Moriya, S. A. Filla, S. Masamune, Angew. Chem. 1995, 107, 869-871
40. Angew. Chem. Int. Ed. Engl. 1995, 34, 793-795
41. A. Abiko, S. Masamune, Tetrahedron Lett. 1996, 37, 1081-1084.
42. J. W. Hill, W. H. Carothers, J. Am. Chem. Soc. 1933, 55, 5039-5043.
43. Discovery Studio 3.0-advanced software package for life science researchers, Accelrys, Inc., San Diego, CA 92121, 2010. For more information, see.
44. Gaussian03, Revision E.01, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery,Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Wallingford CT, 2004.
45. H. B. Schlegel, J. Comput. Chem. 1982, 3, 214-218.
46. J. Dale, Acta Chem. Scand. 1973, 27, 1115-1129.