Total syntheses of graphisin A and sydowinin B

Organic Letters

Volumn 14, Issue 11, 2012, Pages 2862-2865

  Little, Andrew ^a   Porco, John A ^a  

^a USA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENONE DERIVATIVE; GRAPHISIN A; SYDOWININ B; XANTHONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

BENZOPHENONES; CYCLIZATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; XANTHONES;

EID: 84861832056     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301107m     Document Type: Article

References (49)

1. Presented in part at the 240th American Chemical Society National Meeting, Aug 22-26, 2010, Boston; abstract ORGN 410.
2. Isaka, M.; Palasarn, S.; Auncharoen, P.; Komwijit, S.; Jones, E. B. Tetrahedron Lett. 2008, 50, 284-287
3. Tabata, N.; Tomoda, H.; Matsuzaki, K.; Omura, S. J. Am. Chem. Soc. 1993, 115, 8558-8564
4. He, H.; Bigelis, R.; Solum, E.; Carter, G. J. Antibiot. 2003, 56, 923-930
5. Milat, M. L.; Praange, T.; Ducrot, P. H.; Tabet, J. C.; Einhorn, J.; Blein, J. P.; Lallelmand, J. Y. J. Am. Chem. Soc. 1992, 114, 1478-1479
6. Jalal, M. A.; Hossain, M. B.; Robeson, D. J.; Helm, D. J. Am. Chem. Soc. 1992, 114, 5967-5971
7. Pittayakhajonwut, P.; Sri-indrasutdhi, V.; Dramae, A.; Lapanun, S.; Suvannakad, R.; Tantichareon, M. Aust. J. Chem. 2009, 62, 389-391
8. Hamasaki, T.; Sato, Y.; Hatsuda, Y. Agr. Biol. Chem. 1975, 39, 2341-2345
9. Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402-8403
10. Kaiser, F.; Schwink, L.; Velder, J.; Schmalz, H. G. J. Org. Chem. 2002, 67, 9248-9256
11. Slavov, N.; Cvengros, J.; Neudorfl, J. M.; Schmalz, H. G. Angew. Chem., Int. Ed. 2010, 49, 7588-7591
12. Hollinshead, S. P.; Nichols, J. B.; Wilson, J. W. J. Org. Chem. 1994, 59, 6703-6709
13. Clarke, H. T.; Taylor, E. R. Org. Synth. Collect. 1943, 2, 588
14. Jeso, V.; Nicolaou, K. C. Tetrahedron Lett. 2009, 50, 1161-1163
15. Sousa, M. E; Pinto, M. M. Curr. Med. Chem. 2005, 12, 2447-2479
16. Diderot, N. T.; Silvere, N.; Etienne, T. Adv. Phytomed. 2006, 2, 273-298
17. Pinto, M. M. M.; Castanheiro, R. A. P. Nat. Prod. 2009, 520-675
18. Brennfuhrer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114-4133
19. Tschaen, D. M.; Desmond, R.; King, A. O; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synth. Commun. 1994, 24, 887-890
20. Katritzky, A. R.; Pilarski, B.; Urogdi, L. Synthesis 1989, 12, 949-950
21. Booth, B. L.; Jibodu, K. O.; Proenca, M. F. J. Chem. Soc., Perkin Trans. 1 1983, 1067-1068
22. Jayachitra, G.; Yasmeen, N.; Srinivasa, K.; Ralte, S. L.; Singh, A. K. Synth. Commun. 2003, 33, 3461-3466
23. Srinivasan, R.; Rao, K. S.; Jayachitra, G.; Ralte, S. L. Synth. Commun. 2006, 36, 2883-2886
24. Luo, F. T.; Jeevanadam, A. Tetrahedron Lett. 1998, 39, 9455-9456
25. Anzalone, L.; Hirsch, J. A. J. Org. Chem. 1985, 50, 2128-2133
26. Storm, J. P.; Andersson, C. M. J. Org. Chem. 2000, 65, 5264-5274
27. Staab, H. A.; Hauck, R.; Popp, B. Eur. J. Org. Chem. 1998, 1, 631-642
28. Lindstrom, U. Green Chem. 2006, 8, 22-24
29. For Zn(II)-mediated dehydration of amides in water, see: Manjula, K.; Pasha, M. A. Synth. Commun. 2007, 37, 1545-1550
30. Goddard, M. L.; Tabacchi, R. Tetrahedron Lett. 2006, 47, 909-911
31. Yu, M.; Snider, B. B. Org. Lett. 2011, 13, 4224-4227
32. Zhang, W.; Krohn, K.; Flörke, U.; Pescitelli, G.; Di Bari, L.; Antus, S.; Kurtan, T.; Rheinheimer, J.; Draeger, S.; Schulz, B. Chem.-Eur. J. 2008, 14, 4913-4923
33. Gerard, E. M. C.; Bräse, S. Chem.-Eur. J. 2008, 14, 8086-8089
34. Qin, T.; Johnson, R. P.; Porco, J. A. J. Am. Chem. Soc. 2011, 133, 1714-1717
35. Kurobane, I.; Vining, L. C. Tetrahedron Lett. 1978, 16, 1379-1382
36. Kurobane, I.; Vining, L. C.; McInnes, A. C. J. Antibio. 1979, 1256-1266
37. Bräse, S.; Encinas, A.; Keck, J.; Nising, C. F. Chem. Rev. 2009, 109, 3903-3990
38. Franck, B.; Stockigt, U.; Franckowiak, G. Chem. Ber. 1973, 106, 1198-1220
39. Nicolaou, K. C.; Li, A. Angew. Chem., Int. Ed. 2008, 120, 6681-6684
40. Bröhmer, M. C.; Bourcet, E.; Nieger, M.; Bräse, S. Chem.-Eur. J. 2011, 17, 13706-13711
41. Tisdale, E. J.; Kochman, D. A.; Theodorakis, E. A. Tetrahedron Lett. 2003, 44, 3281-3284
42. Suzuki, Y.; Fukuta, Y.; Ota, S.; Kamiya, M.; Sato, M. J. Org. Chem. 2011, 76, 3960-3967
43. Hendrickson, J. B.; Ramsay, M. V. J.; Kelly, T. R. J. Am. Chem. Soc. 1972, 94, 6834-6843
44. Lewis, J. R.; Paul, J. G. J. Chem. Soc., Perkin Trans. 1 1981, 770-775
45. Adeboya, M. O.; Edwards, R. L.; Lassoe, T.; Maitland, D. J.; Shields, S.; Whalley, A. J. S. J. Chem. Soc., Perkin Trans. 1 1996, 1419-1426
46. Andrus, M. B.; Hicken, E. J.; Meredith, E. L.; Simmons, B. L.; Cannon, J. F. Org. Lett. 2003, 5, 3859-3862
47. Gao, W.; He, Z.; Qian, Y.; Zhao, J.; Huang, Y. Chem. Sci. 2012, 3, 883-886
48. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734
49. For examples of cyclization of hindered 2-hydroxybenzoyl- p- quinones to xanthones, see: Nichols, A. L.; Zhang, P.; Martin, S. F. Org. Lett. 2011, 13, 4696-4699