Microwave-assisted regioselective synthesis of natural 6-prenylpolyhydroxyisoflavones and their hydrates with hypervalent iodine reagents

Tetrahedron

Volumn 62, Issue 36, 2006, Pages 8625-8635

  Hossain, Mohammad M ^a   Kawamura, Yasuhiko ^a   Yamashita, Kazuyo ^a   Tsukayama, Masao ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

3 Iodochalcones; 6 Prenylisoflavones; Derrubone; Hypervalent iodine; Lupisoflavone; MW synthesis; Regioselectivity; Wighteone

Indexed keywords

2 METHYL 3 BUTYN 2 OL; 6 PRENYLPOLYHYDROXYISOFLAVONE DERIVATIVE; [BIS(TRIFLUOROACETOXY)IODO]BENZENE; [HYDROXY(TOSYLOXY)IODO]BENZENE; ACETAL DERIVATIVE; CHALCONE DERIVATIVE; CHEMICAL COMPOUND; DERRUBONE; IODINE; IODINE DERIVATIVE; ISOFLAVONE DERIVATIVE; LUPISOFLAVONE; PALLADIUM; REAGENT; UNCLASSIFIED DRUG; WIGHTEONE;

ARTICLE; CATALYSIS; CYCLIZATION; DEHYDRATION; HYDROGENATION; HYDROLYSIS; MICROWAVE RADIATION; OXIDATION; PRIORITY JOURNAL;

EID: 33746319983     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.06.066     Document Type: Article

References (41)

1. Gedye R., Smith F., Westaway K., Ali H., Baldisera L., Laberge L., and Rousell J. Tetrahedron Lett. 27 (1986) 279-282
2. Giguere R.J., Bray T.L., and Duncan S.M. Tetrahedron Lett. 27 (1986) 4945-4948
3. Gedye R.N., Smith F.E., and Westaway K.C. Can. J. Chem. 66 (1988) 17-26
4. Loupy A., Petit A., Hamelin J., Texier-Boullet F., Jacquault P., and Mathé D. Reviews-Update. Synthesis (1998) 1213-1233
5. Strauss C.R., and Trainor R.W. Invited Review. Aust. J. Chem. 48 (1995) 1665-1692
6. Verma R.S. Green Chem. (1999) 43-55
7. Dewic P.M. In: Harborne J.B. (Ed). The Flavonoids: Advances in Research since 1986 (1992), Chapman and Hall, London 117-238
8. Ingham J.L. In: Hertz W., Grisebach H., and Kirby G.W. (Eds). Progress in the Chemistry of Organic Natural Products Vol. 43 (1983), Springer, New York, NY 1-266
9. Ingham J.L., Keen N.T., and Hymowitz T. Phytochemistry 16 (1977) 1943-1946
10. Middleton Jr. E., and Kandaswami C. In: Harborne J.B. (Ed). The Flavonoids: Advances in Research Since 1986 (1992), Chapman and Hall, London 619-652
11. Lang'at-Thoruwa C., Song T.T., Hu J., Simons A.L., and Murphy P.A. J. Nat. Prod. 66 (2003) 149-151
12. McCue P., and Shetty K. Crit. Rev. Food Sci. Nutr. 44 (2004) 361-367
13. Kulling S.E., Honig D.M., and Metzler M. J. Agric. Food Chem. 49 (2001) 3024-3033
14. Murata M., Midorikawa K., Koh M., Umezawa K., and Kawanishi S. Biochemistry 43 (2004) 2569-2577
15. Harborne J.B., Ingham J.L., King L., and Payne M. Phytochemistry 15 (1976) 1485-1487
16. Deshpande V.H., Pendse A.D., and Pendse R. Indian J. Chem., Sect. B 15 (1977) 205-207
17. Ingham J.L., Tahara S., and Harborne J.B. Z. Naturforsch., C: Biosci. 38 (1983) 194-200
18. Tahara S., Ingham J.L., Nakahara S., Mizutani J., and Harborne J.B. Phytochemistry 23 (1984) 1889-1900
19. Tahara S., Nakahara S., Ingham J.L., and Mizutani J. Nippon Nôgeik. Kaishi 59 (1985) 1039-1044
20. Hossain M.M., Tokuoka T., Yamashita K., Kawamura Y., and Tsukayama M. Synth. Commun. 36 (2006) 1201-1211
21. Tsukayama M., Li H., Nishiuchi M., Takahashi M., and Kawamura Y. J. Chem. Res., Synop. (1998) 238-239
22. J. Chem. Res., Miniprint (1998) 1181-1196
23. Al-Maharik N., and Botting N.P. Tetrahedron 59 (2003) 4177-4181
24. Barcelo A.R., and Munoz R. Phytochemistry 28 (1989) 1331-1333
25. East A.J., Ollis W.D., and Wheeler R.E. J. Chem. Soc. C (1969) 365-374
26. Johnson A.P., and Pelter A. Tetrahedron Lett. 20 (1964) 1267-1274
27. Ollis W.D., Rhodes C.A., and Sutherland I.O. Tetrahedron 23 (1967) 4741-4760
28. Falshaw C.P., Ollis W.D., Moore J.A., and Magnus K. Tetrahedron (1966) 333-348
29. Jain A.C., and Jain S.M. Tetrahedron 28 (1972) 5063-5067
30. Várady J. Tetrahedron Lett. 48 (1965) 4273-4275
31. Tsukayama M., Kawamura Y., Tamaki H., Kubo T., and Horie T. Bull. Chem. Soc. Jpn. 62 (1989) 826-832
32. Farkas L., Gottsegen A., Nórgrádi M., and Antus S. J. Chem. Soc., Perkin Trans. 1 (1974) 305-312
33. Dewic P.M. In: Harborne J.B., and Mabry T.J. (Eds). The Flavonoids: Advances in Research (1982), Chapman and Hall, London 535-640
34. Tsukayama M., Wada H., Kawamura Y., Yamashita K., and Nishiuchi M. Chem. Pharm. Bull. 52 (2004) 1285-1289
35. Moriarty R.M., Khosrowshahi J.S., and Prakash O. Tetrahedron Lett. 26 (1985) 2961-2964
36. Miki Y., Fujita R., and Matsushita K. J. Chem. Soc., Perkin Trans. 1 (1998) 2533-2536
37. Kawamura Y., Maruyama M., Tokuoka T., and Tsukayama M. Synthesis 17 (2002) 2490-2496
38. Varvoglis A. Hypervalent Iodine in Organic Synthesis (1997), Academic, London pp 9-15
39. Ahluwalia V.K., Prakash C., and Jolly R.S. J. Chem. Soc., Perkin Trans. 1 (1981) 1697-1702
40. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 50 (1975) 4467-4470
41. Erdélyi M., and Gogoll A. J. Org. Chem. 66 (2001) 4165-4169