A new route to the synthesis of pyranoflavone and pyranochalcone natural products and their derivatives

Synthesis

Volumn , Issue 4, 2006, Pages 603-608

  Lee, Yong Rok ^a   Kim, Do Hoon ^a  

^a Yeungnam University   (South Korea)

Author keywords

tubaic acid; 2H pyran; Desmethyl isoencecalin; Isoencecalin; Pyranochalcones; Pyranoflavones

Indexed keywords

CARBOXYLIC ACIDS; REACTION KINETICS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

2H-PYRAN; DESMETHYL ISOENCECALIN; ISOENCECALIN; PYRANOCHALCONES; PYRANOFLAVONES; TUBAIC ACID;

KETONES;

4 HYDROXYLONCHOCARPIN; 4 HYDROXYLONCHOCARPIN DERIVATIVE; BETA TUBAIC ACID; CHALCONE DERIVATIVE; FLAVONE DERIVATIVE; ISOENCECALIN; LONCHOCARPIN; LONCHOCARPIN DERIVATIVE; NATURAL PRODUCT; NORISOENCECALIN; PYRANOCHALCONE DERIVATIVE; PYRANOFLAVONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG ACTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33644514681     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926294     Document Type: Article

References (45)

1. (a) Wagner, H.; Farkas, L. In The Flavonoids; Harorne, J. B.; Mabry, T. J.; Mabry, H., Eds.; Academic Press: New York, 1975, 127.
2. (b) Gripenberg, J. In The Chemistry of Flavonoid Compounds; Geissman, T. A., Ed.; MacMillan: New York, 1962, 409.
3. (c) Wollenweber, E. In The Flavonoids; Harborne, J. B., Ed.; Chapman & Hall: London, 1994, 259.
4. (d) In The Handbook of Natural Products, Vol. 2; Harborne, J. B.; Baxter, H., Eds.; John Wiley & Sons Ltd.: London, 1999, 1.
5. (a) Magalhães, A. F.; Azevedo Tozzi, A. M. G.; Noronha Sales, B. H. L.; Magalhães, E. G. Phytochemistry 1996, 42, 1459.
6. (b) Magalhães, A. F.; Tozzi, A. M. A.; Magalhães, E. G.; Nogueira, M. A.; Queiroz, S. C. N. Phytochemistry 2000, 55, 787.
7. Banerji, A.; Luthria, D. L.; Prabhu, B. R. Phytochemistry 1988, 27, 3637.
8. (a) Chan, S.-C.; Ko, H.-H.; Lin, C.-N. J. Nat. Prod. 2003, 66, 427.
9. (b) Wang, Y.-H.; Hou, A.-J.; Chen, L.; Chen, D.-F.; Sun, H.-D.; Zhao, Q.-S.; Bastow, K. F.; Nakanish, Y.; Wang, X.-H.; Lee, K.-H. J. Nat. Prod. 2004, 67, 757.
10. Fang, N.; Casida, J. E. J. Nat. Prod. 1999, 62, 205.
11. (a) Saini, T. R.; Pathak, V. P.; Khanna, R. N. J. Nat. Prod. 1983, 46, 936.
12. (b) Pathak, V. P.; Saini, T. R.; Khanna, R. N. Phytochemistry 1983, 22, 1303.
13. (c) Subrahmanyam, K.; Madhusudhana Rao, V.; Jagannadha Rao, K. V. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1997, 15, 12.
14. (a) Welton, A. F.; Tobias, L. D.; Fiedler-Nagy, C.; Anderson, W.; Hope, W.; Meyers, K.; Coffey, J. W. In Plant Flavonoids in Biology and Medicine; Cody, V.; Middleton, E. Jr.; Harbone, J. B., Eds.; Alan R. Liss Inc.: New York, 1986, 231.
15. (b) Demizu, S.; Kajiyama, K.; Hiraga, Y.; Kinoshida, T.; Koyama, K.; Takahashi, K.; Tamura, Y.; Okada, K.; Kinoshida, T. Chem. Pharm. Bull. 1992, 40, 392.
16. (c) Haraguchi, H.; Tanimoto, K.; Tamura, Y.; Mizutani, K.; Kinoshita, T. Phytochemistry 1998, 48, 125.
17. (d) Mitscher, L. A.; Park, Y. H.; Clark, D.; Beal, J. L. J. Nat. Prod. 1980, 43, 259.
18. (e) Nishino, H.; Yoshioko, K.; Iwashima, A.; Takizawa, H.; Konishi, S.; Okamoto, H.; Pkabe, H.; Shibata, S.; Fujiki, H.; Sugimura, T. Jpn. J. Cancer Res. 1986, 77, 33.
19. (f) Okada, K.; Tamura, Y.; Yamamoto, M.; Inoue, Y.; Takagaki, R.; Takahashi, K.; Demizu, S.; Kajiyama, K.; Hiraga, Y.; Kinoshita, T. Chem. Pharm. Bull. 1989, 37, 2528.
20. (g) van Marie, J.; Arasen, P. N.; Lind, A.; van Weeren-Kramer, J. Eur. J. Pharmacol. 1981, 72, 219.
21. (h) Zani, F.; Cuzzoni, M. T.; Daglia, M.; Benvenuti, S.; Vampa, G.; Mazza, P. Planta Med. 1993, 59, 502.
22. (a) Yu, D.; Chen, C.-H.; Brossi, A.; Lee, K.-H. J. Med. Chem. 2004, 47, 4072.
23. (b) Tan, W.; Li, W.-D. Z.; Huang, C.; Li, Y. Synth. Commun. 1999, 29, 3369.
24. (c) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem. Int. Ed. 2000, 39, 734.
25. (d) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barleenga, S.; Mitchell, H. J., J. Am. Chem. Soc. 2000, 122, 9939.
26. (e) Narender, T.; Gupta, S. Bioorg. Med. Chem. Lett. 2004, 14, 3913.
27. (a) Lee, Y. R.; Kweon, H. I.; Koh, W. S.; Min, K. R.; Kim, Y.; Lee, S. H. Synthesis 2001, 1851.
28. (b) Lee, Y. R.; Kim, D. H.; Shim, J.-J.; Kim, S. K.; Park, J. H.; Cha, J. S.; Lee, C.-S. Bull. Korean Chem. Soc. 2002, 23, 998.
29. Allan, J.; Robinson, R. J. Chem. Soc., Trans. 1924, 125, 2192.
30. (a) Baker, W. J. Chem. Soc. 1933, 1381.
31. (b) Madal, H. S.; Venkataraman, K. J. Chem. Soc. 1934, 1767.
32. (a) Iinuma, M.; Iwashima, K.; Matsuura, S. Chem. Pharm. Bull. 1984, 32, 4935.
33. (b) Hoshino, Y.; Oohinata, T.; Takeno, N. Bull. Chem. Soc. Jpn. 1986, 59, 2351.
34. (a) Hercouet, A.; LeCorre, M.; LeFloc'h, Y. Synthesis 1982, 597.
35. (b) LeFloc'h, Y.; LeFeuvre, M. Tetrahedron Lett. 1986, 27, 5503.
36. von Strandtmann, M.; Klutchko, S.; Cohen, M. P.; Shavel, J. J. Heterocycl. Chem. 1972, 9, 171.
37. Yoshihiko, O.; Hiromichi, M.; Katsura, M. Agric. Biol. Chem. 1976, 40, 1245.
38. (a) Ahluwalia, V. K.; Jolly, R. S.; Tehim, A. K. Tetrahedron 1982, 38, 3673.
39. (b) Nickl, J. Chem. Ber. 1958, 91, 1372.
40. Kulkarni, M. M.; Nagasampagi, B. A.; Deshpande, S. G.; Sharma, R. N. Phytochemistry 1987, 26, 2969.
41. Agarwal, S. K.; Verma, S.; Singh, S. S.; Tripathi, A. K.; Khan, Z. K.; Kumar, S. J. Ethnopharm. 2000, 71, 231.
42. (a) Ahluwalia, V. K.; Arora, K. K. Tetrahedron 1981, 37, 1437.
43. (b) Jain, A. C.; Lal, P.; Seshadri, T. R. Indian J. Chem. 1969, 7, 1072.
44. Luyengi, L.; Lee, I.-S.; Mar, W.; Fong, H. H. S.; Pezzuto, J. M.; Kinghorn, A. G. Phytochemistry 1994, 36, 1523.
45. Mukerjee, S. K.; Sarkar, S. C.; Seshadri, T. R. Indian J. Chem. 1970, 8, 861.