Browse > Article
http://dx.doi.org/10.5012/bkcs.2012.33.8.2647

Concise Synthetic Approaches to Naturally Occurring β-Hydroxypyranochalcones: First Total Synthesis of Purpurenone, Its Derivative, and Praecansone B  

Wang, Xue (School of Chemical Engineering, Yeungnam University)
Lee, Yong-Rok (School of Chemical Engineering, Yeungnam University)
Kim, Sung-Hong (Analysis Research Division, Daegu Center, Korea Basic Science Institute)
Publication Information
Abstract
The total synthesis of biologically interesting ${\beta}$-hydroxypyranochalcones, purpurenone (1), its derivative 2, praecansone B (3), and pongapinone A (4) has been accomplished starting from commercially available 2,4-dihydroxyacetophenone or 6-methoxy-2,4-dihydroxyacetophenone in 3 steps by a convergent strategy through benzopyran formations, O-methylations, and coupling reactions.
Keywords
${\beta}$-Hydroxypyranochalcone; Purpurenone; Praecansone B; Pongapinone A; Benzopyran formation;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 0  (Related Records In Web of Science)
연도 인용수 순위
1 Nakahira, H.; Sunagawa, M. Tetrahedron Lett. 1997, 38, 4443.   DOI
2 Lee, Y. R.; Kim, D. H. Synthesis 2006, 603.
3 Lee, Y. R.; Xia, L. Synthesis 2007, 3240.
4 Lee, Y. R.; Choi, J. H.; Yoon, S. H. Tetrahedron Lett. 2005, 46, 7539.   DOI
5 Lee, Y. R.; Lee, W. K.; Noh, S. K.; Lyoo, W. S. Synthesis 2006, 853.
6 Lee, Y. R.; Kim, J. H. Synlett. 2007, 2232.
7 Wang, X.; Lee, Y. R. Tetrahedron Lett. 2007, 48, 6275.   DOI
8 Lee, Y. R.; Li, X.; Kim, J. H. J. Org. Chem. 2008, 73, 4313.   DOI
9 Hari, G. S.; Lee, Y. R. Bull. Korean Chem. Soc. 2011, 32, 2949.   DOI
10 Lim, D.; Zhou, G.; Livanos, A. E.; Fang, F.; Coltart, D. M. Synthesis 2008, 2148.
11 Rao, M. S.; Rao, P. S.; Toth, G.; Balazs, B.; Duddeck, H. J. Nat. Prod. 1998, 61, 1148.   DOI
12 Krohn, K.; Steingrover, K.; Rao, M. S. Phytochemistry 2002, 61, 931.   DOI
13 Narender, T.; Tanvir, S. K.; Rao, M. S.; Srivastava, K.; Puri, S. K. Bioorg. Med. Chem. Lett. 2005, 15, 2453.   DOI
14 Welton, A. F.; Tobias, L. D.; Fiedler-Nagy, C.; Anderson, W.; Hope. W.; Meyers, K.; Coffey, J. W. In Plant Flavnoids in Biology and Medicine
15 Narender, T.; Gupta, S.; Gupta, S. Bioorg. Med. Chem. Lett. 2004, 14, 3913.   DOI
16 Miranda, C. L.; Stevens, J. F.; Helmrich, A.; Henderson, M. C.; Rodriguez, R. J.; Yang, Y.-H.; Deinzer, M. L. Barnes, D. W.; Buhler, D. R. Food Chem. Toxicol. 1999, 37, 271.   DOI   ScienceOn
17 Han, A.-R.; Kang, Y.-J.; Windono, T.; Lee, S. K.; Seo, E.-K. J. Nat. Chem. 2006, 69, 719.
18 Demizu, S.; Kajiyama, K.; Hiraga, Y.; Kinoshida, T.; Koyama, K.; Takahashi, K.; Tamura, Y.; Okada, K.; Kinoshida, T. Chem. Pharm. Bull. 1992, 40, 392.   DOI
19 Magalhaes, A. F.; Tozzi, A. M. G. A.; Sales, B. H. L. N.; Magalhaes, E. G. Phytochemistry 1996, 42, 1459.   DOI
20 Magalhaes, A. F.; Tozzi, A. M. G. A.; Magalhaes, E. G.; Sannomiya, M.; Soriano, M. D. P. C.; Perez, M. A. F. An Acad. Bras. Cienc. 2007, 79, 351.   DOI
21 Tarus, P. K.; Machacho, A. K.; Lang'at-Thoruwa, C. C.; Chhabra, S. C. Phytochemistry 2002, 60, 375.   DOI
22 Kokwaro, J. O. Medicinal Plants of East Africa; East African Literature Bureau: Nairobi, 1993; p 250.
23 Gillet, J. B.; Polhill, R. M.; Verdcourt, B. Flora of Tropical East Africa; The Government Printers: Nairobi, 1071; p 501.
24 Kitagawa, I.; Zhang, R.-S.; Hori, K.; Tsuchiya, K.; Shibuya, H. Chem. Pharm. Bull. 1992, 40, 2041.   DOI
25 In The Handbook of Natural Products; Harborne, J. B., Baxter, H., Eds.; John Wiley & Sons Ltd.: London, 1999; Vol 2, p 1.
26 Wagner, H.; Farkas, L. In The Flavonoids; Harorne, J. B., Mabry, T. J., Mabry, H., Eds.; Academic Press: New York, 1975; p 127.
27 Gripenberg, J. In The Chemistry of Flavonoid Compounds; Geissman, T. A., Ed.; MacMillan: New York, 1962; p 409.
28 Wollenweber, E. In The Flavonoids; Harborne, J. B., Ed.; Chapman & Hall: London, 1994; p 259.
29 Fang, N.; Casida, J. E. J. Nat. Prod. 1999, 62, 205.   DOI
30 Saini, T. R.; Pathak, V. P.; Khanna, R. N. J. Nat. Prod. 1983, 46, 936.
31 Pathak, V. P.; Saini, T. R.; Khanna, R. N. Phytochemistry 1983, 22, 1303.   DOI
32 Subrahmanyam, K.; Madhusudhana Rao, V.; Jagannadha Rao, K. V. Indian J. Chem. 1997, 15B, 12.