Utility of Weitz' aminium salt for obtaining quinones as potential synthetic precursors of quassinoids

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 4, 1997, Pages 613-619

  Takeya, Tetsuya ^a   Motegi, Satoru ^a   Itoh, Toshimasa ^a   Tobinaga, Seisho ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

oxidation; quassinoid; quinone; synthesis; synthon; Weitz'aminium salt

Indexed keywords

AMINE; ANTIMONY DERIVATIVE; INDANONE DERIVATIVE; PHENOL DERIVATIVE; QUASSINOID DERIVATIVE; QUINONE DERIVATIVE; REAGENT; SILANE DERIVATIVE; TRITERPENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGHER PLANT; OXIDATION; STEREOCHEMISTRY;

EID: 0030948957     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.613     Document Type: Article

References (30)

1. a) Fujita S., Yuki Gosei Kagaku Kyokai Shi, 40, 307-320 (1982);
2. b) Swenton J. S., Acc. Chem. Res., 16, 74-80 (1983).
3. Takeya T., Yamaki S., Itoh T., Hosogai H., Tobinaga S., Chem. Pharm. Bull., 44, 909-918 (1996).
4. a) Bell F. A., Ledwith A., Sherrington D. C., J. Chem. Soc., (C), 1969, 2719-2720;
5. b) Kricka L., Ledwith A., J. Chem. Soc., Perkin Trans. 1, 1973, 294-297;
6. c) Schmidt W., Steckham E., Angew. Chem. Int. Ed. Engl., 17, 673-674 (1978);
7. d) Bellville D. J., Wirth D. D., Bauld N. L., ibid., 103, 718-720 (1981);
8. e) Pabon R. A., Bellville D. J., Bauld N. L., ibid., 106, 2730-2731 (1984);
9. f) Kluge R., Sivilai L., Kamm B., Tetrahedron, 46, 2371-2380 (1990);
10. g) Bauld N. L., Mirafzal G. A., J. Am. Chem. Soc., 113, 3613-3614 (1991);
11. h) Mirafzal H., Liu A., Bauld J. N. L., ibid., 115, 6072-6077 (1993):
12. i) Schulz M., Dhanalekshmi S., Venkatachalam C. S., Balasubramanian K. K., J. Chem. Soc., Chem. Commun., 1994, 511-512;
13. j) Takeya T., Ara Y., Tobinaga S., Chem. Pharm. Bull., 43, 1970-1976 (1995);
14. k) idem. ibid., 43, 1977-1984 (1995).
15. a) Kupchan S. M., Britton R. W., Lacadie J. A., Ziegler M. F., Sigel C. W., J. Org. Chem., 40, 648-652 (1975):
16. b) Polonsky J., "Progress in the Chemistry of Organic Natural Products," Vol. 47, ed. by Springer-Verlag, Berlin, 1985, pp. 221-264.
17. a) Zakharkin L. I., Khorlina I. M., Tetrahedron Lett., 14, 619-623 (1962);
18. b) Mandel L., Lee D. E., Courtney L. F., J. Org. Chem., 47, 610-615 (1982).
19. a) Seebach D., Leher F., Angew. Chem. Int. Ed. Engl., 15, 505-511 (1976);
20. b) Wollenberg R. H., Miller S. J., Tetrahedron Lett., 35, 3219-3223 (1976);
21. c) Gilbert B. C., Norman R. O. C., J. Chem. Soc., 60, 1379-1385 (1982);
22. d) Rosini G., Ballini R., Synthesis, 1988, 833-847;
23. e) Rosini G., Trost B. M., Fleming I., "Comprehensive Organic Synthesis," Vol. 2, ed. by Heathcock C. H., Pergamon Press, Oxford, 1991, pp. 239-275.
24. 4 in the presence of silica gel from the corresponding nitrostyrene, which was prepared by the condensation of benzylisovanillin and nitroethane with ethylenediammonium diacetate.
25. T-5b was not purified from the mixture of E-5b and T-5b.
26. a) Collington E. W., Finch H., Smith I. J., Tetrahedon Lett., 26, 681-684 (1985);
27. b) Schimittling E. A., Sawyer J. S., Tetrahedon Lett., 32, 7207-7210 (1991).
28. Murase M., Kotani E., Okazaki K., Tobinaga S., Chem. Pharm. Bull., 31, 3159-3162 (1986).
29. a) Yoshida J., Maekawa T., Murata T., Matsunaga S., J. Am. Chem. Soc., 112, 1962-1970 (1990);
30. b) Yoshida J., Yuki Gosei Kagaku Kyokai Shi, 53, 53-63 (1995).