An expeditious synthesis of methyl jasmonate

Helvetica Chimica Acta

Volumn 89, Issue 6, 2006, Pages 1258-1264

  Chapuis, Christian ^a   Cantatore, Carole ^a   De Saint Laumer, Jean Yves ^a  

^a Analysis and Perception Department   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; OZONIZATION; SYNTHESIS (CHEMICAL);

DIELS-ALDER CYCLOADDITION; OZONOLYSIS;

AROMATIC COMPOUNDS;

5 CHLORO 2,3,3A,47,7A HEXAHYDRO 1H INDEN 1 ONE; ALDEHYDE; CHLOROPRENE; CYCLOPENT 2 ENONE; JASMONIC ACID METHYL ESTER; METHYL [3 OXO 2 (2 OXOETHYL)CYCLOPENTYL]ACETATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; EPIMER; OZONOLYSIS; PRIORITY JOURNAL; SYNTHESIS; WITTIG REACTION;

EID: 33745744119     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200690124     Document Type: Article

References (64)

1. C. Chapuis, G. Büchi, H. Wüest, Helv. Chim. Acta 2005, 88, 3069;
2. C. Chapuis, H. Wüest, to Firmenich SA, WO 2004043895, March 27, 2004 (Chem. Abstr. 2004, 141, 6855j).
3. H. Tanaka, S. Torii, J. Org. Chem., 1975, 40, 462.
4. J.-Q. Yu, H.-C. Wu, E. J. Corey, Org. Lett. 2005, 7, 1415;
5. K. C. Nicolaou, T. Montagnon, P. S. Baran, Angew. Chem., Int. Ed. 2002, 41, 1386;
6. Y. Shvo, A. H. I. Arisha, J. Org. Chem. 1998, 63, 5640;
7. T. T. Wenzel, J. Chem. Soc., Chem. Commun. 1989, 932;
8. M. Korach, D. R. Nielsen, W. H. Rideout, Org. Synth. Coll. Vol. V 1973, 414.
9. E. Dane, K. Eder, Ann. 1939, 539, 207;
10. R. Granger, P. F. G. Nau, C. François, Bull. Soc. Chim. Fr. 1962, 1902;
11. H. O. House, G. H. Rasmusson, J. Org. Chem. 1963, 28, 31.
12. a) F. Fringuelli, F. Pizzo, A. Taticchi, T. D. J. Hall, E. Wenkert, J. Org. Chem. 1982, 47, 5056;
13. b) F. Fringuelli, F. Pizzo, A. Taticchi, E. Wenkert, Synth. Commun. 1979, 9, 391;
14. B. Maurer, A. Hauser, Helv. Chim. Acta 1982, 65, 462.
15. H. C. Hailes, B. Isaac, M. Hashim Javaid, Tetrahedron 2001, 57, 10329.
16. E. W. Garbisch, J. Org. Chem. 1965, 30, 2109.
17. R. Braun, J. Sauer, Chem. Ber. 1986, 119, 1269;
18. P. A. Grieco, J. J. Nunes, M. D. Gaul, J. Am. Chem. Soc. 1990, 112, 4595;
19. P. A. Grieco, Aldrichim. Acta 1991, 24, 59;
20. P. A. Grieco, J. P. Beck, Tetrahedron Lett. 1993, 34, 7367.
21. R. Kumareswaran, P. S. Vankar, M. V. P. Reddy, S. V. Pitre, R. Roy, Y. D. Vankar, Tetrahedron 1999, 55, 1099.
22. B. G. Reddy, R. Kumareswaran, Y. D. Vankar, Tetrahedron Lett. 2000, 41, 10333.
23. H. C. Hailes, in 'Advances in Flavours and Fragrances', Ed. K. A. D. Swift, Royal Society of Chemistry, 2002, p. 127.
24. M. Matsui, K. Mori, T. Ogawa, T. Kitahara, Y. Warita, to T. Hasegawa Perfumery, Ltd., JP53-108950, March 3, 1977 (Chem. Abstr. 1979, 90, 54562);
25. M. Matsui, K. Mori, T. Ogawa, T. Kitahara, Y. Katsuta, to T. Hasegawa Perfumery, Ltd., JP61-017531, June 3, 1985 (Chem. Abstr. 1986, 105, 114647).
26. M. E. Jung, D. Ho, H. V. Chu, Org. Lett. 2005, 7, 1649.
27. T. Kitahara, K. Mori, M. Matsui, M. Iwamoto, Y. Takagi, Y. Warita, Agric. Biol. Chem. 1982, 46, 1369.
28. C. W. Bird, H. J. Butler, M. P. L. Caton, E. C. J. Coffee, C. J. Hardy, T. W. Hart, H. J. Mason, Tetrahedron Lett. 1985, 26, 4101;
29. C. W. Brid, H. I. Butler, M. P. L. Caton, E. C. J. Coffee, to May & Baker, Ltd., GB2121410, May 26, 1983 (Chem. Abstr. 1984, 101, 406932).
30. H.-J. Liu, W. M. Feng, Synth. Commun. 1987, 17, 1777;
31. H. J. Liu, W. M. Feng, J. B. Kim, E. N. C. Browne, Can. J. Chem. 1994, 72, 2163.
32. T. K. Sarkar, B. K. Ghorai, J. Indian Chem. Soc. 1999, 76, 693.
33. SPARTAN 02, Wave Function, Inc., Irvine, CA 92612, U.S.A.
34. I. Fleming, 'Frontier Orbitals and Organic Chemical Reactions', J. Wiley, Chichester, New York, Brisbane, Toronto, 1976.
35. H. L. Gordon, S. Freeman, T. Hudlicky, Synlett 2005, 19, 2911.
36. Y. Kimura, M. Suzuki, T. Matsumoto, R. Abe, S. Terashima, Bull. Chem. Soc. Jpn. 1986, 59, 415;
37. Y. Kimura, M. Suzuki, T. Matsumoto, R. Abe, S. Terashima, Chem. Lett. 1984, 473;
38. H. K. Hall, P. Nogues, J. W. Rhoades, R. C. Sentman, M. Detar, J. Org. Chem. 1982, 47, 1451;
39. R. G. Hall, S. Trippett, Tetrahedron Lett. 1982, 23, 2603;
40. R. Riemschneider, P. Claus, Monatsh. Chem. 1962, 93, 844;
41. W. J. Middleton, R. E. Heckert, E. L. Little, C. G. Krespan, J. Am. Chem. Soc. 1958, 80, 2783;
42. S. J. Averill, H. L. Trumbull, J. Am. Chem. Soc. 1954, 76, 1159;
43. J. Doucet, P. Rumpf, Bull. Soc. Chim. Fr. 1954, 21, 610;
44. J. S. Meek, W. B. Trapp, J. Am. Chem. Soc. 1952, 74, 2686;
45. A. Korolev, V. Mur, Zh. Obshch. Khim. 1948, 18, 1977
46. (Chem. Abstr. 1949, 43, 3797e);
47. A. Korolev, V. Mur, Doklady Akad. Nauk SSSR 1948, 59, 251
48. (Chem. Abstr. 1948, 42, 6776f);
49. W. Carothers, I. Williams, A. M. Collins, J. E. Kirby, J. Am. Chem. Soc. 1931, 53, 4203.
50. H. Keul, K. Griesbaum, Can. J. Chem. 1980, 58, 2049 ;
51. K. Griesbaum, H. Keul, Angew. Chem. 1975, 87, 748.
52. S. Blechert, C. Bockelmann, O. Brummer, M. Füsslein, H. Grundlach, G. Haider, S. Holder, T. M. Kutchan, E. W. Weiler, M. H. Zenk, J. Chem. Soc., Perkin Trans. 1 1997, 3549;
53. H. Kiyota, M. Saitoh, T. Oritani, T. Yoshihara, Phytochem. 1996, 42, 1259;
54. T. Kitahara, M. Iwamoto, Y. Takagi, K. Mori, M. Matsui, Agric. Biol. Chem. 1984, 1731.
55. H. Matsuura, F. Ohmori, M. Kobayashi, A. Sakurai, T. Yoshihara, Biosci. Biotechnol Biochem. 2000, 64, 2380;
56. O. Miersch, Z. Naturforsch., B 1991, 46, 1727.
57. T. Ainai, M. Matsuumi, Y. Kobayashi, J. Org. Chem. 2003, 68, 7825;
58. M. Matsui, K. Mori, T. Ogawa, T. Kitahara, Y. Warita, to T. Hasegawa Perfumery, Ltd., JP53-108949, March 3, 1977 (Chem. Abstr. 1979, 90, 86853).
59. B. Schaub, Ph.D. Thesis, University of Basel, Switzerland, March 5, 1985, p. 115.
60. E. J. Corey, Angew. Chem., Int. Ed. 2002, 41, 1650;
61. D. H. Ryu, T. W. Lee, E. J. Corey, J. Am. Chem. Soc. 2002, 124, 9992;
62. K. Futatsugi, H. Yamamoto, Angew. Chem., Int. Ed. 2005, 44, 1484;
63. H. Yamamoto, K. Futatsugi, Angew. Chem., Int. Ed. 2005, 44, 1924.
64. C. Chapuis, M. Barthe, J.-Y de Saint Laumer, Helv. Chim. Acta 2001, 84, 230.