Syntheses and odor descriptions of cyclopropanated compounds part 5. Analogs of methyl jasmonate to fix the relative configuration of the two side chains

Helvetica Chimica Acta

Volumn 87, Issue 7, 2004, Pages 1854-1859

  Kiyota, Hiromasa ^a   Takigawa, Shin Ya ^a   Kuwahara, Shigefumi ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIFFUSION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CYCLOPROPANATED COMPOUNDS; ENOL ACETATE; STEREOCHEMICAL PROPERTIES;

ODOR CONTROL;

CYCLOPROPANE; JASMONIC ACID; JASMONIC ACID METHYL ESTER; METHYL EPIJASMONATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLOPROPANATION; DRUG SYNTHESIS; GEOMETRY; ODOR; ORCHIDACEAE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 4043096159     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200490164     Document Type: Article

References (23)

1. H. Kiyota, T. Takai, S. Kuwahara, Flavour Fragr. J. 2003, 18, 100.
2. a) A. Yoshioka, T. Yamada, J. Synth. Org. Chem. Jpn. (in Japanese) 1990, 18, 56 (Chem. Abstr. 1990, 113, 117376v);
3. a) A. Yoshioka, T. Yamada, J. Synth. Org. Chem. Jpn. (in Japanese) 1990, 18, 56 (Chem. Abstr. 1990, 113, 117376v);
4. b) F. Näf, R. Decorzant, Helv. Chim. Acta 1978, 61, 2524.
5. G. Fráter, J. A. Bajgrowicz, P. Kraft, Tetrahedron 1998, 54, 7633.
6. E. Demole, E. Lederer, D. Mercier, Helv. Chim. Acta 1962, 45, 675.
7. R. Nishida, T. E. Acree, H. Fukami, Agric. Biol. Chem. 1985, 49, 769.
8. a) H. Kiyota, E. Higashi, T. Koike, T. Oritani, Flavour Fragr. J. 2001, 16, 175;
9. b) Kiyota, T. Koike, E. Higashi, T. Oritani, Flavour Fragr. J. 2002, 17, 267;
10. c) H. Kiyota, E. Higashi, T. Takai, T. Oritani, S. Kuwahara, Flavour Fragr. J. 2002, 17, 227.
11. a) H. Kiyota, Y. Yoneta, T. Oritani, Phytochemistry 1997, 46, 983;
12. b) U. Ravid, R. Ikan, J. Org. Chem. 1974, 39, 2637;
13. c) J. L. Ward, P. Gaskin, M. H. Beale, R. Sessions, Y. Koda, C. Wasternack, Tetrahedron 1997, 53, 8181.
14. T. Taapken, S. Blechert, E. W. Weiler, M. H. Zenk, J. Chem. Soc., Perkin Trans. 1 1994, 1439.
15. H. Kiyota, M. Saitoh, T. Oritani, T. Yoshihara, Phytochemistry 1996, 42, 1259.
16. a) R. A. J. Kaiser, in 'Bioactive Volatile Compounds from Plants', Eds., R. Teranishi, R. G. Buttery, H. Sugisawa, Oxford Univ. Press, New York 1993, ACS Symposium Series, Vol. 525, p. 240;
17. b) T. Kitahara, M. Inoue, S. Tamogami, R. Kaiser, Tetrahedron 1996, 52, 1487.
18. a) R. Kaiser, D. Lamparsky, Tetrahedron Lett. 1974, 38, 3413;
19. b) P. Ducos, F. Rouessac, Tetrahedron 1973, 29, 3233;
20. c) S. Torii, H. Tanaka, Y. Kobayashi, J. Org. Chem. 1977, 42, 3473;
21. d) M. Hatanaka, Y. Himeda, Y. Tanaka, I. Ueda, Tetrahedron Lett. 1995, 36, 3211.
22. H. E. Simmons, T. L. Cairns, S. A. Vladuchick, C. M. Hoiness, Org. React. 1973, 20, 1.
23. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155.