Further explorations into the synthesis of Dehydro-Hedione®

Helvetica Chimica Acta

Volumn 96, Issue 2, 2013, Pages 246-258

  Winter, Béat ^a   Chapuis, Christian ^a   Brauchli, Robert ^a   De Saint Laumer, Jean Yves ^a  

^a Analysis and Perception Department   (Switzerland)

Author keywords

Dehydrohedione; Epoxidation; Hedione; Jasmonate; Paradisone; Reformatsky reaction

Indexed keywords

DEHYDROHEDIONE; HEDIONE; JASMONATES; PARADISONE; REFORMATSKY REACTION;

EPOXIDATION; ETHERS; PARAFFINS; PROPANE;

ORGANIC COMPOUNDS;

3 CHLOROPERBENZOIC ACID; ALCOHOL DERIVATIVE; ALLYL ALCOHOL; CYCLOPROPANE; DEHYDROHEDIONE; DICHLOROMETHANE; ETHER; INDUSTRIAL CHEMICAL; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CATALYSIS; CIS ISOMER; ELIMINATION REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REFORMATSKY REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84874083681     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201200440     Document Type: Article

References (94)

1. P. Dubs, R. Stüssi, Helv. Chim. Acta 1978, 61, 998
2. C. Chapuis, G. H. Büchi, H. Wüest, Helv. Chim. Acta 2005, 88, 3069
3. T. Shono, M. Okawa, I. Nishiguchi, J. Am. Chem. Soc. 1975, 97, 6144
4. K. Crawford, V. Rautenstrauch, A. Uijttewaal, Synlett 2001, 1127
5. K. Sisido, S. Kurozumi, K. Utimoto, Perfum. Essent. Oil Rec. 1969, 60, 267)
6. U. Ravid, R. Ikan, J. Org. Chem. 1974, 39, 2637
7. U. Ravid, R. Ikan, R. M. Sachs, J. Agric. Food. Chem. 1975, 23, 835
8. B. Winter, to Firmenich SA, US5302745, 12 Apr. 1994 (Chem. Abstr. 1994, 120, 269718)
9. T. Shono, N. Kise, Tetrahedron Lett. 1990, 31, 1303
10. T. Shono, N. Kise, T. Fujimoto, N. Tominaga, H. Morita, J. Org. Chem. 1992, 57, 7175
11. D. Anderson, G. Frater, to Givaudan-Roure SA, EP953562, 03 Nov. 1999 (Chem. Abstr. 1999, 131, 324143)
12. F. Näf, R. Decorzant, to Firmenich SA, US5760277, 2 Jun. 1998 (Chem. Abstr. 1997, 126, 143920).
13. S. Katsuya, M. Fumio, to Asahi Kasei Chem. Co., WO2007/4442, 11 Jan. 2007 (Chem. Abstr. 2007, 146, 142304)
14. T. Yamada, H. Fujisawa, H. Tanaka, to Nippon Zeon, EP399788, 25 Aug. 1989 (Chem. Abstr. 1990, 114, 163600)
15. P. Teisseire, M. Plattier, to Roure-Bertrand & Dupont, FR7046407, 23 Dec. 1970 (Chem. Abstr. 1972, 78, 3798)
16. D. A. Dobbs, K. P. M. Vanhessche, E. Brazi, V. Rautenstrauch, J.-Y. Lenoir, J.-P. Genêt, J. Wiles, S. H. Bergens, Angew. Chem., Int. Ed. 2000, 39, 1992
17. V. Rautenstrauch, K. P. M. Vanhessche, J. P. Genêt, J. Y. Lenoir, to Firmenich SA, US5874600, 23 Feb. 1999 (Chem. Abstr. 1997, 127, 183071)
18. D. Dobbs, K. P. M. Vanhessche, V. Rautenstrauch, to Firmenich SA, US6214763, 10 Apr. 2001 (Chem. Abstr. 1998, 130, 40076)
19. T. Ebata, K. Matsumoto, H. Matsushita, Heterocycles 1994, 38, 2231
20. M. Hamberg, O. Miersch, G. Sembdner, Lipids 1988, 23, 521
21. O. Miersch, A. Preiss, G. Sembdner, K. Schreiber, Phytochemistry 1987, 26, 1037
22. R. K. Hill, A. G. Edwards, Tetrahedron 1965, 21, 1501.
23. E. Demole E. Lederer, to Firmenich SA, CH382731, 25 Feb. 1960
24. E. Demole E. Lederer, to Firmenich SA, CH490313, 27 Jul. 1960 (Chem. Abstr. 1970, 73, 109368)
25. A. Firmenich, R. Firmenich, G. Firmenich, R. E. Firmenich, to Firmenich SA, CH382731, 24 Feb. 1961 (Chem. Abstr. 1963, 58, 3038).
26. E. Demole, E. Lederer, D. Mercier, Helv. Chim. Acta 1962, 45, 675
27. E. Demole, E. Lederer, D. Mercier, Helv. Chim. Acta 1962, 45, 685
28. E. Demole, M. Stoll, Helv. Chim. Acta 1962, 45, 692.
29. W. Renold, R. Näf-Muller, U. Keller, B. Willhalm, G. Ohloff, Helv. Chim. Acta 1974, 57, 1301
30. L. G. Kharebava, A. G. Tsirgvava, Chai. Kul'tura I Pr-vo, Tbilisi 1979, 2, 26, (Chem. Abstr. 1979, 92, 162361)
31. A. G. Sardzhveladze, I. A. Chernavina, L. G. Kharebava, Subtrop. Kul't. 1985, 6, 78, (Chem. Abstr. 1985, 104, 206166).
32. P. Werkhoff, G. Krammer, S. Brennecke, M. Roloff, H.-J. Bertram, Food Rev. Int. 2002, 18, 103
33. R. Näf, in 'Citrus Oils, Composition, Advanced Analytical Techniques, Contaminants, and Biological Activity', Eds. G. Dugo, L. Mondello, CRC Press, London, 2011, p. 463.
34. O. Cresp, J. Cavallier, P.-A. Blanc, A. Morillas, Perfum. Flavor. 2011, 36(11), 24
35. A. Boix Camps, Perfum. Flavor. 2007, 32(11), 40.
36. E. Demole, 'Fragrance Chemistry, the Science of the Sense of Smell', Ed. E. T. Theimer, Academic Press, New York, 1982, p. 349
37. T. K. Sarkar, B. K. Ghorai, J. Indian Chem. Soc. 1999, 76, 693
38. C. Chapuis, Perfum. Flavor. 2011, 36(12), 36
39. C. Chapuis, Helv. Chim. Acta 2012, 95, 1479.
40. M. F. Ansell, J. W. Ducker, J. Chem. Soc. 1959, 329
41. K. Oshima, H. Yamamoto, H. Nozaki, J. Am. Chem. Soc. 1973, 95, 4446
42. M. L. Roumestant, M. Malacria, J. Goré, J. Grimaldi, M. Bertrand, Synthesis 1976, 755
43. V. Rautenstrauch, to Firmenich SA, US4499297, 12 Feb. 1985 (Chem. Abstr. 1984, 101, 170776).
44. B. M. Trost, A. B. Pinkerton, Org. Lett. 2000, 2, 1601
45. B. M. Trost, A. B. Pinkerton, J. Org. Chem. 2001, 66, 7714
46. B. M. Trost, A. B. Pinkerton, J. Am. Chem. Soc. 2002, 124, 7376.
47. J.-M. Vatèle, Synlett. 2008, 1785
48. J.-M. Vatèle, Tetrahedron, 2010, 66, 904.
49. A. Eschenmoser, US3939207, 17 Feb. 1976 (Chem. Abstr. 1971, 75, 484341)
50. A. Barco, S. Benetti, G. P. Pollini, R. Taddia, Synthesis 1975, 104
51. T. Punniyamurthy, B. Bhatia, M. M. Reddy, G. C. Madhava, J. Iqbal, Tetrahedron 1997, 53, 7649
52. E. Delort, A. Velluz, E. Frérot, M. Rubin, A. Jacquier, M. Rubin, S. Linder, K. F. Eidman, B. S. Mac Dougall, J. Agric. Food. Chem. 2011, 59, 11752.
53. H. Baltz, B. Bierling, K. Kirschke, H. Oberender, M. Schultz, DD81650, 5 May 1971 (Chem. Abstr. 1973, 78, 99214)
54. K. Blau, U. Müller, W. Pritzkow, W. Schmidt-Renner, Z. Sedshaw, J. Prakt. Chem. 1980, 322, 915
55. S. Uemur, S. R. Patil, Tetrahedron Lett. 1982, 23, 4353
56. S. Uemura, S. R. Patil, Chem. Lett. 1982, 11, 1743
57. anonymous, to Jpn Kokai Tokkyo Koho, JP 5872533, 30 Apr. 1983 (Chem. Abstr. 1983, 99, 87704)
58. anonymous, to Nippon Zeon, JP 5980619, 10 May 1984 (Chem. Abstr. 1984, 101, 151487)
59. M. Uyanik, M. Akakura, K. Ishihara, J. Am. Chem. Soc. 2009, 131, 251.
60. E. Nakamura, J. Shimada, I. Kuwajima, J. Chem. Soc., Chem. Commun. 1983, 498
61. I. Erden, N. Oecal, J. Song, C. Gleason, C. Gärtner, Tetrahedron 2006, 62, 10676.
62. M. M. Kabat, L. M. Garofalo, A. R. Daniewski, S. D. Hutchings, W. Liu, M. Okabe, R. Radinov, Y. Zhou, J. Org. Chem. 2001, 66, 6141
63. B. M. Trost, P. Seoane, S. Mignani, M. Acemoglu, J. Am. Chem. Soc. 1989, 111, 7487.
64. C. Fehr, J. Galindo, Angew. Chem., Int. Ed. 2000, 39, 569
65. Angew. Chem. 2000, 112, 581.
66. K. Fujiwara, H. Sakai, T. Tanaka, M. Hiroma, Chem. Lett. 1994, 23, 457
67. S.-J. Jeon, P. J. Walsh, J. Am. Chem. Soc. 2003, 125, 9544
68. S.-J. Jeon, H. Li, C. Garcia, L. K. LaRochelle, P. J. Walsh, J. Org. Chem. 2005, 70, 448
69. T. J. Snape, Org. Biomol. Chem. 2006, 4, 4144.
70. J. M. Carr, T. S. Snowden, Tetrahedron 2008, 64, 2897.
71. C. Fehr, Angew. Chem. 1998, 110, 2509
72. Angew. Chem., Int. Ed. 1998, 37, 2407.
73. J. Gon Kim, K. M. Waltz, I. F. Garcia, D. Kwiatkowski, P. J. Walsh, J. Am. Chem. Soc. 2004, 126, 12580
74. S.-J. Jeon, H. Li, P. J. Walsh, J. Am. Chem. Soc. 2005, 127, 16416
75. A. J. Wooten, J. G. Kim, P. J. Walsh, Org. Lett. 2007, 9, 381
76. Y.-M. Zao, P. Gu, H.-J. Zhang, Q.-W. Zhang, C.-A. Fan, Y.-Q. Tu, F.-M. Zhang, J. Org. Chem. 2009, 74, 3211.
77. A. G. Myers, M. Hammond, Y. Wu, J.-N. Xiang, P. M. Harrington, E. Y. Kuo, J. Am. Chem. Soc. 1996, 118, 10006
78. A. G. Myers, R. Glatthar, M. Hammond, P. M. Harrington, E. Y. Kuo, J. Liang, S. E. Schaus, Y. Wu, J.-N. Xiang, J. Am. Chem. Soc. 2002, 124, 5380.
79. W. Paget, D. Reichlin, E. C. Walborsky, R. L. Snowden, C. Vial, to Firmenich SA, US 5726345, 10 Mar. 1998 (Chem. Abstr. 1995, 123, 116298).
80. D.-R. Ahn, M. Mosimann, C. J. Leumann, Nucleosides, Nucleotides Nucleic Acids, 2003, 22, 1207
81. D.-R. Ahn, M. Mosimann, C. J. Leumann, J. Org. Chem. 2003, 68, 7693
82. W.-K. Chan, P. Liu, W.-Y. Yu, M.-K. Wong, C.-M. Che, Org. Lett. 2004, 6, 1597
83. E. Elhalem, M. J. Comin, J. B. Rodriguez, Eur. J. Org. Chem. 2006, 4473.
84. A. B. Smith III, M. A. Guaciaro, S. R. Schow, P. M. Wovkulich, B. H. Toder, T. W. Hall, J. Am. Chem. Soc. 1981, 103, 219
85. A. G. Myers, P. M. Harrington, E. Y. Kuo, J. Am. Chem. Soc. 1991, 113, 694
86. T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465.
87. Jaguar, version 7.8, Schrödinger, LLC, New York, NY, 2011
88. J. A. R. Luft, K. Meleson, K. N. Houk, Org. Lett. 2007, 9, 555.
89. M. Ohba, T. Haneishi, T. Fujii, Chem. Pharm. Bull. 1996, 44, 525
90. R. H. Crabtree, M. W. Davis, J. Org. Chem. 1986, 51, 2655.
91. M. Vincens, C. Dumont, M. Vidal, Bull. Soc. Chim. Fr. 1984, II-59.
92. H. Kiyota, S. Takigawa, S. Kuwahara, Helv. Chim. Acta 2004, 87, 1854
93. H.-K. Yim, Y. Liao, H. N. C. Wong, Tetrahedron 2003, 59, 1877.
94. C. Chapuis, M. Barthe, J.-Y. de Saint Laumer, Helv. Chim. Acta 2001, 84, 230.