The first total synthesis of kwakhurin, a characteristic component of a rejuvenating plant, "kwao keur": Toward an efficient synthetic route to phytoestrogenic isoflavones

Organic and Biomolecular Chemistry

Volumn 3, Issue 4, 2005, Pages 674-681

  Ito, Fumihiro ^a   Iwasaki, Misako ^a   Watanabe, Toshiko ^a   Ishikawa, Tsutomu ^a   Higuchi, Yoshihiro ^b  

^a CHIBA UNIVERSITY   (Japan)

^b Shiratori Pharmaceutical Co Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HORMONES; METALLIZING; OXIDATION; PHENOLS; PLANTS (BOTANY); REACTION KINETICS;

KETALIZATION; METHOXYETHOXYMETHYL (MEM); REAGENTS; TETRABYTYLAMMONIUM BROMIDE (TBAB);

DRUG PRODUCTS;

BORONIC ACID DERIVATIVE; CHROMONE DERIVATIVE; FUSED HETEROCYCLIC RINGS; ISOFLAVONE DERIVATIVE; KWAKHURIN; PHYTOESTROGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; OXIDATION REDUCTION REACTION; PUERARIA; SYNTHESIS;

BORONIC ACIDS; CHROMONES; HETEROCYCLIC COMPOUNDS, 3-RING; ISOFLAVONES; METHYLATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHYTOESTROGENS; PUERARIA;

FABACEAE; LATEOLABRAX JAPONICUS; PUERARIA; PUERARIA MIRIFICA;

EID: 14544305986     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b414955f     Document Type: Article

References (34)

1. (a) J. L. Ingham, S. Tahara and G. S. Pope, Pueraria, ed. W. M. Keung, chapter 6, pp. 97-118, Taylor & Francis, London and New York, 2002;
2. (b) J. Cain, Nature, 1960, 188, 774;
3. (c) J. L. Ingham, K. R. Markham and S. Z. Dziedzic, Phytochemistry, 1986, 25, 1772;
4. (d) H. E. M. Jones and G. S. Pope, J. Endocrinol., 1960, 20, 229;
5. (e) H. E. M. Jones, H. B. Waynforth and G. S. Pope, J. Endocrinol., 1961, 22, 293;
6. (f) H. E. M. Jones and G. S. Pope, J. Endocrinol., 1961, 22, 303;
7. (g) W. Cherdshewasart, W. Cheewasopit and P. Picha, J. Ethnopharmacol., 2004, 93, 255;
8. (h) H. Trisomboon, S. Malaivijitnond, G. Watanabe and K. Taya, J. Pharmacol. Sci., 2004, 94, 51.
9. (a) S. Chansakaow, T. Ishikawa, H. Seki, K. Sekine, M. Okada and C. Chaichantipyuth, J. Nat. Prod., 2000, 63, 173;
10. (b) S. Chansakaow, T. Ishikawa, K. Sekine, M. Okada, Y. Higuchi, M. Kudo and C. Chaichantipyuth, Planta Med., 2000, 66, 572.
11. (a) J. L. Ingham, S. Tahara and S. Z. Dziedzic, Z. Naturforsch., C: Biosci., 1986, 41, 403;
12. (b) S. Tahara, J. L. Ingham and S. Z. Dziedzic, Z. Naturforsch., C: Biosci., 1987, 42, 510.
13. -1; detection, 254 nm; injection volume, 20 μL; column temperature, 35°C. [S. Shimokawa, T. Kumamoto, T. Ishikawa, M. Takashi and Y. Higuchi, unpublished result; under these conditions retention time for daizein (3): 27.3 min and for genistein (4): 38.7 min].
14. M. Iwasaki, T. Watanabe, T. Ishikawa, S. Chansakaow, Y. Higuchi and S. Tahara, Heterocycles, 2004, 63, 1375.
15. (a) D. M. X. Donnelly and G. M. Boland, Nat. Prod. Rep., 1995, 12, 321;
16. (b) P. M. Dewick, in The Flavonoids, ed. J. B. Harborne, Chapman and Hall, London, 1994, pp. 117-238.
17. M. Susse, S. Johne and M. Hasse, Helv. Chim. Acta, 1992, 75, 457.
18. R. B. Gammill, Synthesis, 1979, 901.
19. H. Konishi, K. Aritomi, T. Okano and J. Kiji, Bull. Chem. Soc. Jpn., 1989, 62, 591.
20. (a) M. Larhed and A. Hallberg, J. Org. Chem., 1996, 61, 9582;
21. (b) K. Olofsson, A. Hallberg, M. Larhed, in Microwaves in Organic Synthesis, ed. A. Loupy, Wiley-VCH, Weinheim, 2002, pp. 379-403;
22. (c) Y. Xu and Q.-X. Guo, Heterocycles, 2004, 63, 903 and references therein.
23. (a) N. E. Leadbeater and M. Marco, Angew. Chem. Int. Ed., 2003, 42, 1407;
24. (b) N. E. Leadbeater and M. Marco, J. Org. Chem., 2003, 68, 5660.
25. (a) Y. Hoshino, N. Miyaura and A. Suzuki, Bull. Chem. Soc. Jpn., 1988, 61, 3008;
26. (b) A.-S. Castanet, F. Cobolt, J.-R. Desmurs and T. Schlama, J. Mol. Catal. A: Chem., 2002, 182-183, 481.
27. (a)W.G. Dauben, J.M. Cogen and V. Behar, Tetrahedron Lett., 1990, 31, 3241;
28. (b) E. J. Corey and L. I. Wu, J. Am. Chem. Soc., 1993, 115, 9327.
29. M. R. Dintzner, K. M. Morse, K. M. McClelland and D. M. Coligado, Tetrahdron Lett., 2004, 45, 79.
30. F. X. Talamas, D. B. Smith, A. Cervantes, F. Franco, S. T. Culter, D. G. Loughhead, D. J. Morgana, Jr. and R. J. Weikert, Tetrahdron Lett., 1997, 38, 4725.
31. E. J. Tisdale, B. G. Vong, H. Li, S. H. Kim, C. Chowdhury and E. A. Theodorakis, Tetrahedron, 2003, 59, 6873.
32. J. L. Ingham, S. Tahara and S. Z. Dziedzic, Z. Naturforsch., C: Biosci., 1988, 43, 5.
33. A. V. K. Prasad, R. S. Kapil and S. P. Popli, J. Chem. Soc., Perkin Trans. 1, 1986, 1561.
34. S. Chansakaow, PhD Thesis, 2000, Chiba University, Japan.