A short-step synthesis of sesquiterpene lactone, 1-oxoeudesma-2,4-dien-11βh-12, 6α-olide, isolated from artemisia herba-alba and its derivatives

Synthetic Communications

Volumn 26, Issue 1, 1996, Pages 139-148

  Kawamata, T ^a   Nagashima, K ^c   Nakai, R ^c   Tsuji, T ^b  

^a KEIO UNIVERSITY   (Japan)

^b JAPAN WOMEN'S UNIVERSITY   (Japan)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EUDESMANOLIDE DERIVATIVE; SESQUITERPENE LACTONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030023547     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003873     Document Type: Article

References (12)

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2. Gonzalez, A. G. ; Bermejo, J. and Zaragoza, T., Phytochemistry 1983 22, 1509.
3. Marco, J. A. ; Sanz, J. F. ; Falco, E. ; Jakupovic, J. and Lex, J., Tetrahedron 1990, 46, 7941. ; references are cited in.
4. The 35th Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics, Abstract Paper, p 226 (1991), in Nagoya, Japan
5. Miyashita, M. ; Suzuki, T. and Yoshikoshi, A., Chem. Lett. 1987, 2387.
6. The similar type of rearrangement has been reported using artemisinin; Sumi, M. ; Dauben, W. G. and Hayes, W. K. , J. Am. Chem. Soc. 1958, 80, 5704.
7. Huffman, J. W., J. Am. Chem. Soc. 1963, 85, 601.
8. Barrero, A. F. ; Sanchez, J. F. ; Zafra, M. ; Barron, J. A. and Feliciano, A. S., Phytochemistry 1987, 26, 1531.
9. Ando, M. ; Ono, A. and Takase, K., Chem. Lett. 1984, 493.
10. Dauben, W. G. and Michno, D. M., J. Org. Chem. 1977, 42, 682.
11. Bacigaluppo, J. A. ; Colombo, M. I. ; Zinczuk, J., ; Huber, S. N. ; Mischne, M. P. and Ruveda, E. A., Synth. Commun. 1991, 21, 1361.
12. Although the optical rotation of our synthetic material was higher than that reported for natural product, the IR, UV, NMR and MS exactly matched.