Xanthone natural products via N -heterocyclic carbene catalysis: Total synthesis of atroviridin

Journal of Organic Chemistry

Volumn 76, Issue 10, 2011, Pages 3960-3967

  Suzuki, Yumiko ^a   Fukuta, Yoshinori ^a   Ota, Shinya ^a   Kamiya, Masayo ^a   Sato, Masayuki ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROYLATION; CARBENES; FLUOROBENZENE; INTRAMOLECULAR 1 ,4-ADDITION; N-HETEROCYCLIC CARBENES; NATURAL PRODUCTS; TOTAL SYNTHESIS;

CARBON INORGANIC COMPOUNDS; CATALYSIS; CYCLIZATION; ORGANIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

ATROVIRIDIN; BENZOPHENONE DERIVATIVE; CARBENE; HETEROCYCLIC COMPOUND; NATURAL PRODUCT; QUINONE DERIVATIVE; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

AROYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS;

BENZOQUINONES; BIOLOGICAL PRODUCTS; CATALYSIS; HETEROCYCLIC COMPOUNDS; METHANE; XANTHONES;

EID: 79956145718     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200303c     Document Type: Article

References (30)

1. N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, 2006.
2. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309
3. Díe-Gonzále, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874-883
4. Glorius, F., Ed. N-Heterocyclic Carbenes in Transition Metal Catalysis. In Topics in Organometallic Chemistry; Springer-Verlag: Berlin/Heidelberg, 2007; Vol. 28.
5. For reviews, see: Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541
6. Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130-5135
7. Marion, N.; Díe-Gonzále, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988-3000
8. Suzuki, Y.; Toyota, T.; Imada, F.; Sato, M.; Miyashita, A. Chem. Commun. 2003, 1314-1315
9. Suzuki, Y.; Ota, S.; Fukuta, Y.; Ueda, Y.; Sato, M. J. Org. Chem. 2008, 73, 2420-2423
10. For our reviews, see: Suzuki, Y. J. Syn. Org. Chem. Jpn. 2008, 66, 377-386
11. Suzuki, Y. Yakugaku Zasshi 2008, 128, 1179-1185
12. Suzuki, Y.; Toyota, T.; Miyashita, A.; Sato, M. Chem. Pharm. Bull. 2006, 54, 1653-1658
13. 6) ? 27.76, 78.94, 102.28, 103.48, 107.90, 114.91, 119.11, 120.13, 124.68, 125.35, 128.54, 145.10, 148.46, 148.74, 149.08, 153.91, 180.38.
14. For selected examples, see: Asano, J.; Chiba, K.; Tada, M.; Yoshii, T. Phytochemistry 1996, 41, 815-820
15. Iinuma, M.; Ito, T.; Miyake, R.; Tosa, H.; Tanaka, T.; Chelladura, V. Phytochemistry 1998, 47, 1169-1170
16. Okudaira, C; Ikeda, Y.; Konndo, S.; Furuya, S.; Hirabayashi, Y.; Koyano, T.; Saito, Y.; Umezawa, K. J. Enzym. Inhib. 2000, 15, 129-138
17. Suksamraran, S.; Suwannapoch, N.; Phakhodee, W.; Thanuhiranlert, J.; Ratananukul, P.; Chimnoi, N.; Suksamrarn, A. Chem. Pharm. Bull. 2003, 51, 857-859
18. Hamada, M.; Iikubo, K.; Ishikawa, Y.; Ikeda, A.; Umezawa, K.; Nishiyama, S. Bioorg. Med. Chem. Lett. 2003, 13, 3151-3153
19. Sukpondma, Y.; Rukachaisirikul, V.; Phongpaichit, S. Chem. Pharm. Bull. 2005, 53, 850-852
20. Tisdale, E. J.; Kochman, D. A.; Theodorakis, E. A. Tetrahedron Lett. 2003, 44, 3281-3284
21. Knusen, R. D.; Snyder, H. R. J. Org. Chem. 1974, 39, 3343-3346
22. Lee, C-.M.; Parks, J. A.; Bunnell, P. R.; Platner, J. J.; Field, M. J.; Giebisch, G. H. J. Med. Chem. 1985, 28, 589-594
23. Godfrey, J. D., Jr.; Mueller, R. H.; Sedergran, T. C.; Soundararajan, N.; Colandrea, V. J. Tetrahedron Lett. 1994, 35, 6405-6408
24. Quillinan, A. J.; Scheinmann, F. J. Chem. Soc., Perkin Trans. 1 1972, 1382-1387
25. Brown, P. E.; Lewis, R. A.; Waring, M. A. J. Chem. Soc., Perkin Trans. 1 1990, 2979-2988
26. Thurston, D. E.; Murty, V. S.; Langley, D. R.; Jones, G. B. Synthesis 1990, 81-84
27. Felix, A. M.; Heimer, E. P.; Lambros, T. J.; Tzougraki, C.; Meienhofer, J. J. Org. Chem. 1978, 43, 4194-4196
28. For similar examples, see: Pearson, M. S.; Jensky, B. J.; Greer, F. X.; Hagstrom, J. P.; Wells, N. M. J. Org. Chem. 1978, 43, 4617-4622
29. Laatsch, H. Liebigs Ann. Chem. 1980, 140-151
30. Kündig, E. P.; García, A. E.; Lomverget, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 2006, 45, 98-101