Browse > Article
http://dx.doi.org/10.5012/bkcs.2011.32.1.153

Concise Synthesis of (±)-Rhinacanthin A, Dehydro α-Lapachone, and β-Lapachone, and Pyranonaphthoquinone Derivatives  

Wang, Xue (School of Chemical Engineering and Technology, Yeungnam University)
Chen, Ye (School of Chemical Engineering and Technology, Yeungnam University)
Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.1, 2011 , pp. 153-156 More about this Journal
Abstract
A concise synthesis of (${\pm}$)-rhinacanthin A is achieved in two steps by epoxidation of dehydro-$\alpha$-lapachone, followed by chemo- and regioselective reduction. Dehydro-$\alpha$-lapachone was also synthesized in two steps starting from 4-methoxy-1-naphthol by ethylenediamine diaetate (EDDA)-catalyzed benzopyran formation and a CAN-mediated oxidation reaction. $\beta$-Lapachone was synthesized in three steps from 4-methoxy-1-naphthol by benzopyran formation, catalytic hydrogenation, and Jones oxidation. As additional reactions, synthesis of pyranonaphthoquinone derivatives with the pyranokunthone B skeleton has been achieved in a single step from readily available 2-hydroxy-6-methoxy-1,4-naphthoquinone and 2-hydroxy-7-methoxy-1,4-naphthoquinone.
Keywords
Pyranonaphthoquinones; Rhinacanthin A; Dehydro-$\alpha$-lapachone; $\beta$-Lapachone;
Citations & Related Records

Times Cited By Web Of Science : 0  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
  • Reference
1 Thomson, R. H. Naturally Occurring Quinones III, Recent Advances; Chapman and Hall: London, 1987; p 609.
2 Amaral, A. C. F.; Barnes, R. A. J. Heterocycl. Chem. 1992, 29, 1457.   DOI
3 Perez-Sacau, E.; Estevez-Braun, A.; ravelo, A.; Ferro, E.; Tokuda, H.; Mukainaka, T.; Nishino, H. Bioorg. Med. Chem. 2003, 11, 483.   DOI   ScienceOn
4 Singh, P.; Natani, K.; Jain, S.; Arya, K.; Dandia, A. Nat. Prod. Res. 2006, 20, 207.   DOI   ScienceOn
5 Sun, J.; Geiser, A. H.; Frydman, B. Tetrahedron Lett. 1998, 39, 8221.   DOI   ScienceOn
6 Burnett, A. R.; Thomson, R. H. J. Chem. Soc. C 1968, 850.   DOI
7 Alves, G. B. C.; Lopes, R. S. C.; Lopes, C. C.; Snieckus, V. Synthesis 1999, 1875.
8 Manna, S. K.; Gad, Y. P.; Mukhopadhyay, A.; Aggarwal, B. B. Biochem. Pharmacol. 1999, 57, 763.   DOI   ScienceOn
9 Villamil, S. H. F.; Perissimoti, L. J.; Stoppani, A. O. M. Biochem. Pharmacol. 1996, 52, 1875.   DOI   ScienceOn
10 Frydman, B.; Marton, I. J.; Sun, J. S.; Nedi, K.; Witiak, D. T.; Liu, A. A. Cancer Res. 1997, 57, 620.
11 Li, C. J.; Li, Y. Z.; Pinto, A. V.; Pardee, A. B. Proc. Natl. Acad. Sci. USA 1999, 96, 13369.   DOI
12 Ough, M.; Lewis, A.; Bey, E. A.; Gao, J.; Ritchie, J. M.; Bornmann, W. G.; Boothman, D. A.; Oberley, L. W.; Cullen, J. J. Cancer Biol. Ther. 2005, 4, 95.   DOI
13 Bey, E. A.; Bentle, M. S.; Reinicke, K. E.; Dong, Y.; Yang, C. R.; Girard, L.: Minna, J. D.; Bornmann, W. G.; Gao, J.; Boothman, D. A. Proc. Natl. Acad. Sci. U S A 2007, 104, 11832.   DOI   ScienceOn
14 Bentle, M. S.; Bey, E. A.; Dong, Y.; Reinicke, K. E.; Boothman, D. A. J. Mol. Histol. 2006, 37, 203.   DOI   ScienceOn
15 Onegi, B.; Kraft, C.; Kohler, I.; Freund, M.; Jenett-Siems, K.; Siems, K.; Beyer, G.; Melzig, M. F.; Bienzle, U.; Eich, E. Phytochemistry 2002, 60, 39.   DOI   ScienceOn
16 Lee, Y. R.; Lee, W. K. Synth. Commun. 2004, 34, 4537.   DOI   ScienceOn
17 Lee, Y. R.; Choi, J. H.; Trinh, D. T. L.; Kim, N. W. Synthesis 2005, 3026.
18 Kumar, S.; Malachowski, W. P.; DuHadaway, J. B.; LaLonde, J. M.; Carroll, P. J.; Jaller, D.; Metz, R.; Prendergast, G. C.; Muller, A. J. J. Med. Chem. 2008, 51, 1706.   DOI   ScienceOn
19 Nasiri, H. R.; Bolte, M.; Schwalbe, H. Nat. Prod. Res. 2008, 22, 1225.   DOI   ScienceOn
20 Kimachi, T.; Torii, E.; Ishimoto, R.; Sakue, A.; Ju-ichi, M. Tetrahedron: Asymmetry 2009, 20, 1683.   DOI   ScienceOn
21 Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004.   DOI   ScienceOn
22 Chochrek, P.; Wicha, J. Org. Lett. 2006, 8, 2551.   DOI   ScienceOn
23 Cho, J. Y.; Kim, H. Y.; Choi, G. J.; Jang, K. S.; Lim, H. K.; Lim, C. H.; Cho, K. Y.; Kim, J.-C. Pest Manag. Sci. 2006, 62, 414.   DOI   ScienceOn
24 Joshi, K. C. Planta Med. 1978, 34, 219.   DOI
25 Wurzburger, J.; Leshem, Y. Phytochemistry 1976, 15, 225.
26 Burnett, A. R.; Thomson, R. H. J. Chem. Soc., C 1967, 2100.   DOI
27 Wu, T. S.; Tien, H. J.; Yeh, M. Y.; Lee, K. H. Phytochemistry 1988, 27, 3787.   DOI   ScienceOn
28 de Sousa, J. R.; Silva, G. D. F.; Miyakoshi, T.; Chen, C.-L. J. Nat. Prod. 2006, 69, 1225.   DOI   ScienceOn
29 Woo, H. J.; Park, K.-Y.; Rhu, C.-H. Lee, W. H.; Choi, B. T.; Kim, G. Y.; Park, Y.-M.; Choi, Y. H. J. Med. Food 2006, 9, 161.   DOI   ScienceOn
30 Goncalves, A. M.; Vasconcellos, M. E.; Docampo, R.; Cruz, F. S.; De Souza, W.; Leon, W. Mol. Biochem. Parasitol. 1980, 1, 167.   DOI   ScienceOn
31 Guiraud, P.; Steiman, R.; Campos-Takaki, G.-M.; Seigle-MuMurandi, F.; De Buochberg, M. S. Planta. Med. 1994, 60, 373.   DOI   ScienceOn
32 Docampo, R.; Cruz, F. S.; Boveris, A.; Muniz, R. P. A.; Esquivel, D. M. S. Biochem. Pharmacol. 1979, 28, 723.   DOI   ScienceOn
33 Boothman, D. A.; Pardee, A. B. Proc. Natl. Acad. Sci. USA 1989, 86, 4963.   DOI
34 Li, C. J.; Pardee, A. B. Cancer Res. 1995, 55, 3712.
35 Planchon, S. M.; Wuerzberger, S.; Frydman, B.; Witiak, D. T.; Hutson, P.; Church, D. R.; Wilding, G.; Bootman, D. A. Cancer Res. 1995, 55, 3706.
36 Li, C. J.; Zhang, L. J.; Dezube, B. J.; Grumpacker, C. J.; Pardee, A. B. Proc. Natl. Acad. Sci. USA 1993, 90, 1839.   DOI   ScienceOn
37 Schuerch, A. R.; Werrli, G. Eur. J. Biochem. 1978, 84, 197.   DOI   ScienceOn