Synthesis and biological activities of degraded limonoids, (±)-fraxinellonone and its related compounds

Tetrahedron Letters

Volumn 38, Issue 2, 1997, Pages 263-266

  Okamura, Hiroaki ^a   Yamauchi, Keiko ^a   Miyawaki, Keiji ^a   Iwagawa, Tetsuo ^a   Nakatani, Munehiro ^a  

^a KAGOSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LIMONOID;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; DRUG TOXICITY; FISH; INSECT; NONHUMAN; REACTION ANALYSIS;

EID: 0031012432     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02277-0     Document Type: Article

References (27)

1. As a review of the biologically active limonoids, see: D. E. Champagne, O. Koul, M. B. Isman, G. G. E. Scudder, and G. H. N. Towers, Photochemistry 1992, 31, 377-394.
2. To our knowledge, only five naturally occurring degraded limonoids are known at present. a) fraxinellonone, J. Boustie, C. Moulis, J. Gleye, I. Fouraste, P. Servin, and M. Bon, Phytochemistry 1990, 29, 1699-1701;
3. b) fraxinellone, M. Pailer, G. Shaden, G. Spiteller, and W. Fenzl, Monatsh. Chem. 1965, 96, 1324-1346; P. Coggon, A. T. McPhail, R. Storer, and D. W. Young, Chem. Commun. 1969, 828;
4. b) fraxinellone, M. Pailer, G. Shaden, G. Spiteller, and W. Fenzl, Monatsh. Chem. 1965, 96, 1324-1346; P. Coggon, A. T. McPhail, R. Storer, and D. W. Young, Chem. Commun. 1969, 828;
5. c) isofraxinellone, A. J. Blaise and F. Winternitz, Phytochemistry 1985, 24, 2379-2381;
6. d) dictamdiol, C. Hu, J. Han, J. Zhao, G. Song, Y. Li, and D. Yin, Zhiwu Xuebao 1989, 31, 453-458; J. Boustie, J. Gleye, A. Blaise, and I. Fouraste, Planta Med. 1992, 58, 228;
7. d) dictamdiol, C. Hu, J. Han, J. Zhao, G. Song, Y. Li, and D. Yin, Zhiwu Xuebao 1989, 31, 453-458; J. Boustie, J. Gleye, A. Blaise, and I. Fouraste, Planta Med. 1992, 58, 228;
8. e) calodendrolide, J. M. Cassady and C. S. Liu, J. Chem. Soc., Chem. Commun. 1972, 86-87.
9. a) Y. Fukuyama, T. Tokoroyama, and T. Kubota, Tetrahedron Lett. 1972, 3401-3404;
10. b) T. Tokoroyama, Y. Fukuyama, T. Kubota, and K. Yokotani, J. Chem. Soc., Perkin Trans. 1 1981, 1557-1562;
11. c) T. Tokoroyama, Y. Kotsuji, H. Matsuyama, T. Shimura, K. Yokotani, and Y. Fukuyama, J. Chem. Soc., Perkin Trans. 1 1990, 1745-1752.
12. d) Y. Fukuyama, T. Tokoroyama, and T. Kubota, Tetrahedron Lett. 1973, 4869-4872;
13. e) T. Tokoroyama, Y. Fukuyama, and Y. Kotsuji, J. Chem. Soc. Perkin Trans. 1 1988, 445-450;
14. f) S. E. Drewes, P. A. Grieco, and J. C. Huffman, J. Org. Chem. 1985, 50, 1309-1311;
15. g) D. Friedrich and L. A. Paquette, J. Org. Chem. 1991, 56, 3831-3840;
16. h) A. F. Mateos and J. A. F. Blanco, J. Org. Chem. 1991, 56, 7084-7092;
17. i) M. Renoud-Grappin, C. Vanucci, and G. Lhommet, J. Org. Chem. 1994, 59, 3902-3905.
18. Compound 4 was synthesized by a similar method with that employed for the preparation of Wieland-Miescher ketone derivative, see: H. J. Liu and T. Dieck-Abularach, Heterocycles 1987, 25, 245-249.
19. Preparation of 2-methyl-3-oxo-butanolide, see: Beilslein, 17, 412.
20. Satisfactory spectral data were obtained for all synthetic intermediates.
21. Relative stereochemistry of 5 was determined from NOE between the signals corresponding to 6-H and pseudo axial 4β-H.
22. Y. Fukuyama, Y. Kawashima, T. Miwa, and T. Tokoroyama, Synthesis 1974, 443-444.
23. E. J. Corey and S. Knapp, Tetrahedron Lett. 1976, 3667-3668.
24. 13C NMR spectra with those of natural product after derivation to (±)-l.
25. M. Fetizon, M. Golfier, P. Mourgues, and J. M. Louis, "Organic Synthesis by Oxidation with Metal Compounds", ed. by W. J. Mijis and C.R.H. I. de Jonge, Plenum Press, 1986, 503-567.
26. 3) δ 175.6, 143.7, 139.9, 127.4, 123.6, 121.2, 108.8, 80.0, 51.2, 41.7, 28.9, 22.0, 21.8, 21.0.
27. K. Wada and K. Munakata, J. Agr. Food. Chem. 1968, 17, 471-474.