Synthesis of both the enantiomers of methyl cis-(Z)-dehydrojasmonate, principal note for the scent of Cymbidium goeringii, to determine the absolute configuration

Tetrahedron

Volumn 52, Issue 5, 1996, Pages 1487-1492

  Kitahara, Takeshi ^a   Inoue, Munenori ^a   Tamogami, Shigeyuki ^b   Kaiser, Roman ^c  

^a UNIVERSITY OF TOKYO   (Japan)

^b T Hasegawa Co   (Japan)

^c GIVAUDAN SCHWEIZ AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDROJASMONIC ACID; FLAVORING AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG IDENTIFICATION; DRUG SYNTHESIS; ENANTIOMER; GAS CHROMATOGRAPHY; PRIORITY JOURNAL;

EID: 0030021007     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00998-1     Document Type: Article

References (11)

1. T. Kitahara, S. -H. Kang, S. Tamogami and R. Kaiser, Nat. Prod. Lett., 1994, 5, 157-164.
2. R. Kaiser, The scent of orchids: Olfactory and chemical investigations, Elsevier, Amsterdam, 1993, pp 150-152, 211-212.
3. T. Kitahara, T. Nishi and K. Mori, Tetrahedron, 1991, 47, 6999-7006.
4. T. Nishi and T. Kitahara, Proc. Japan Acad. Ser. B, 1995, 71, 20-23.
5. H. Tanaka and S. Torii, J. Org. Chem., 1975, 40, 462-465.
6. 2O. In our hands, however, substantial amount of the corresponding hydroxy ester was accompanied, and thus the resulting mixture was submitted to further cyclization step.
7. K. C. Nicolaou, K. Raja Reddy, Golfo Skokatas, Fuminori Sato, Xiao-Yi Xiao, and C. -K. Hwang, J. Am. Chem. Soc., 1993, 115, 3558-3575.
8. D. B. Dess and J. C. Martin, J. Org. Chem., 1983, 48, 4155-4156.
9. 3,4 we adopted PDC oxidation reported by Helmchen et al. (see reference cited below) and obtained excellent results without epimerization. But in this case, the product is extremely susceptible to epimerization and/or polymerization during work up, and we found Dess-Martin oxidation was better choice for this labile product. G. Helmchen, A. Greeke, G. Lauer, M. Urmann and J. Fries, Angew. Chem. Int. Ed. Engl., 1990, 29, 1024-1025.
10. Spectral data of authentic samples were kindly provided by Dr. Y. Takai and Dr. Y. Warita, T. Hasegawa Co. Ltd. It is deeply acknowledged.
11. W. A. König, B. Gehrcke, D. Icheln, P. Evens, J. Dönneche and W. Wang, J. High Res. Chromatog., 1992, 15, 367-372.