Aryne insertion reactions leading to bioactive fused quinazolinones: Diastereoselective total synthesis of cruciferane

Organic Letters

Volumn 15, Issue 15, 2013, Pages 4006-4009

  Vaidya, Sagar D ^a   Argade, Narshinha P ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; CRUCIFERANE; QUINAZOLINE DERIVATIVE; QUINAZOLINONE DERIVATIVE; TRYPTANTHRINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; MOLECULAR STRUCTURE; QUINAZOLINES; QUINAZOLINONES; STEREOISOMERISM;

EID: 84881236848     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4018062     Document Type: Article

References (46)

1. Demeununck, M.; Baussanne, I. Curr. Med. Chem. 2013, 20, 794
2. Liu, X.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem., Int. Ed. 2009, 48, 348
3. Roy, A. D.; Subramanian, A.; Roy, R. J. Org. Chem. 2006, 71, 382
4. Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787 and references cited therein
5. Amin, A. H.; Mehta, D. R.; Samarth, S. S. Prog. Drug. Res. 1970, 14, 218
6. Johne, S. Prog. Drug. Res. 1982, 26, 259
7. Johne, S. Prog. Chem. Org. Nat. Prod. 1984, 46, 159
8. Sinha, S.; Srivastava, M. Prog. Drug. Res. 1994, 43, 143
9. Xie, H.; Zhang, Y.; Zhang, S.; Chen, X.; Wang, W. Angew. Chem., Int. Ed. 2011, 50, 11773
10. Li, L.; Ge, J.; Wu, H.; Xu, Q.-H.; Yao, S. Q. J. Am. Chem. Soc. 2012, 134, 12157 and references cited therein
11. Haynes, S. W.; Gao, X.; Tang, Y.; Walsh, C. T. J. Am. Chem. Soc. 2012, 134, 17444
12. Zhichkin, P.; Kesicki, E.; Treiberg, J.; Bourdon, L.; Ronsheim, M.; Ooi, H. C.; White, S.; Judkins, A.; Fairfax, D. Org. Lett. 2007, 9, 1415
13. Hart, D. J.; Magomedov, N. A. J. Am. Chem. Soc. 2001, 123, 5892
14. He, F.; Foxman, B. M.; Snider, B. B. J. Am. Chem. Soc. 1998, 120, 6417
15. Larraufie, M.-H.; Courillon, C.; Ollivier, C.; Lacoîte, E.; Malacria, M.; Fensterbank, L. J. Am. Chem. Soc. 2010, 132, 4381
16. Giri, R.; Lam, J. K.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 686
17. Xiao, Z.; Yang, M. G.; Li, P.; Carter, P. H. Org. Lett. 2009, 11, 1421
18. Toumi, M.; Couty, F.; Marrot, J.; Evano, G. Org. Lett. 2008, 10, 5027
19. Zhang, C.; De, C. K.; Mal, R.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 416
20. Snider, B. B.; Wu, X. Org. Lett. 2007, 9, 4913
21. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 12, 1211
22. Dubrovskiy, A. V.; Markina, N. A.; Larock, R. C. Org. Biomol. Chem. 2013, 11, 191
23. Bhojgude, S. S.; Biju, A. T. Angew. Chem., Int. Ed. 2012, 51, 1520
24. Gampe, C. M.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3766
25. Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550
26. Chen, Y.; Larock, R. C. In Modern Arylation Methods; Ackerman, J., Ed.; Wiley/VCH: New York, 2009; pp 401-473.
27. Peña, D.; Pérez, D.; Guitián, E. Angew. Chem., Int. Ed. 2006, 45, 3579 and references cited therein
28. Hendrick, C. E.; McDonald, S. L.; Wang, Q. Org. Lett. 2013, 15, 3444
29. Yun, S. Y.; Wang, K.-P.; Lee, N.-K.; Mamidipalli, P.; Lee, D. J. Am. Chem. Soc. 2013, 135, 4668
30. Goetz, A. E.; Garg, N. K. Nature Chem. 2013, 5, 54
31. Hoye, T. R.; Baire, B.; Niu, D.; Willoughby, P. H.; Woods, B. P. Nature 2012, 490, 208
32. Kshirsagar, U. A.; Argade, N. P. Org. Lett. 2010, 12, 3716
33. Tucker, A. M.; Grundt, P. ARKIVOC 2012, No. i, 546
34. Bergman, J.; Lindström, J.-O.; Tilstam, U. Tetrahedron 1985, 41, 2879
35. Jao, C.-W.; Lin, W.-C.; Wu, Y.-T.; Wu, P.-L. J. Nat. Prod. 2008, 71, 1275
36. Chen, M.; Gan, L.; Lin, S.; Wang, X.; Li, L.; Li, Y.; Zhu, C.; Wang, Y.; Jiang, B.; Jiang, J.; Yang, Y.; Shi, J. J. Nat. Prod. 2012, 75, 1167
37. Danz, H.; Stoyanova, S.; Wippich, P.; Brattström, A.; Hamburger, M. Planta Med. 2001, 67, 411
38. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881
39. Gompper, R.; Breitschaft, W. Angew. Chem. 1983, 95, 727
40. Kraus, G. A.; Guo, H. J. Org. Chem. 2009, 74, 5337
41. Zhou, H. B.; Liu, G. S.; Yao, Z. J. J. Org. Chem. 2007, 72, 6270
42. Bergman, J.; Brynolf, A. Tetrahedron 1990, 46, 1295
43. Tadross, P. M.; Gilmore, C. D.; Bugga, P.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2010, 12, 1224
44. Heaney, H. Chem. Rev. 1962, 62, 81
45. Dhokale, R. A.; Thakare, P. R.; Mhaske, S. B. Org. Lett. 2012, 14, 3994
46. Bergman, J.; Tilstam, U.; Törnroos, K.-W. J. Chem. Soc., Perkin Trans. 1 1987, 519