Oxidative rearrangement of pentaalkoxychalcones with phenyl-iodine(III) bis(trifluoroacetate) (PIFA): Synthesis of (±)-10-bromopterocarpin and (±)-pterocarpin

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1998, Pages 2533-2536

  Miki, Yasuyoshi ^a   Fujita, Rie ^a   Matsushita, Ko Ichi ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748648203     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803561j     Document Type: Article

References (17)

1. W. Friedrichsen, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon, New York, 1984, vol. 4, p. 998.
2. T. A. Engler, K. O. Lynch Jr., J. P. Reddy and G. S. Gregory, Bioorg. Med. Chem. Lett., 1993, 3, 1229;
3. T. A. Engler, W. Chai and K. O. LaTessa, J. Org. Chem., 1996, 61, 9297.
4. L. Farkas, À. Gottsegen and M. Nógrádi, J. Chem. Soc., Perkin Trans, 1, 1974, 305.
5. K. Thakkar and M. Cushman, J. Org. Chem., 1995, 60, 6499;
6. T. Horie, K. Shibata, K. Yamashita, K. Fujii, M. Tsukayama and Y. Ohtsuru, Chem. Pharm. Bull., 1998, 46, 222.
7. R. A. Lichtenfels, A. L. Coelho and P. R. R. Costa, J. Chem. Soc., Perkin Trans, 1, 1995, 949.
8. R. M. Moriarty, J. S. Khosrowshahi and O. Prakash, Tetrahedron Lett., 1985, 26, 2961.
9. Y. Miki, S. Kobayashi, N. Ogawa and H. Hachiken, Synlett, 1994, 1001 and references cited therein.
10. J. A. Ferreira, J. W. Nel, E. V. Brandt, B. C. B. Bezuidenhoudt and D. Ferreira, J. Chem. Soc., Perkin Trans, 1, 1995, 1049.
11. T. H. Simpson and P. S. Wright, J. Org. Chem., 1961, 26, 4886.
12. 3 for 20 h 2b yielded rearrangement product 3b in 46% yield.
13. Y. Ozaki, K. Mochida and S.-W. Kim, J. Chem. Soc., Chem. Commun., 1988, 374;
14. T. A. Engler, J. P. Reddy, K. D. Combrink and D. V. Velde, J. Org. Chem., 1990, 55, 1248.
15. K. Mori and H. Kishida, Liebigs Ann. Chem., 1988, 721.
16. T. A Engler, J. P. Reddy, K. D. Combrink and Q. V. Velde, J. Org. Chem., 1990, 55, 1254.
17. M. Uchiyama and M. Matsui, Agric. Biol. Chem., 1967, 31, 1490.