Cyclizations of enediynes under the action of electrophiles

Chemistry of Heterocyclic Compounds

Volumn 49, Issue 1, 2013, Pages 116-139

  Gulevskaya, A V ^a   Lazarevich, R Yu ^a  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

alkynes; cascade reactions; cyclization; enediynes; polynuclear aromatic compounds

Indexed keywords

EID: 84877589245     PISSN: 00093122     EISSN: 15738353     Source Type: Journal    
DOI: 10.1007/s10593-013-1234-0     Document Type: Review

References (48)

1. K. C. Nicolaou and W.-M. Dai, Angew. Chem., Int. Ed. Engl., 30, 1387 (1991).
2. M. D. Lee, G. A. Ellestad, and D. B. Borders, Acc. Chem. Res., 24, 235 (1991).
3. A. L. Smith and K. C. Nicolaou, J. Med. Chem., 39, 2103 (1996). (Pubitemid 26173245)
4. H. H. Wenk, M. Winkler, and W. Sander, Angew. Chem., Int. Ed., 42, 502 (2003). (Pubitemid 36232245)
5. P. R. Hamann, J. Upeslacis, and D. B. Borders, in: G. M. Cragg, D. G. I. Kingston, and D. J. Newman (editors), Anticancer Agents from Natural Products, CRC Press, Boca Raton (2005), p. 451.
6. I. A. Maretina and B. A. Trofimov, Usp. Khim., 75, 913 (2006). (Pubitemid 44884474)
7. M. C. Joshi and D. S. Rawat, Chem. Biodiversity, 9, 459 (2012).
8. R. R. Jones and R. G. Bergman, J. Am. Chem. Soc., 94, 660 (1972).
9. A. Basak, S. Mandal, and S. S. Bag, Chem. Rev., 103, 4077 (2003).
10. D. S. Rawat and J. M. Zaleski, Synlett, 393 (2004).
11. M. Kar and A. Basak, Chem. Rev., 107, 2861 (2007). (Pubitemid 47162902)
12. I. A. Maretina, Zh. Obshch. Khim., 78, 244 (2008).
13. H. W. Whitlock, Jr., P. E. Sandvick, L. E. Overman, and P. B. Reichardt, J. Org. Chem., 34, 879 (1969).
14. J. D. Bradshaw, D. Solooki, C. A. Tessier, and W. J. Youngs, J. Am. Chem. Soc., 116, 3177 (1994).
15. B. Köhig, W. Pitsch, M. Klein, R. Vasold, M. Prall, and P. R. Schreiner, J. Org. Chem., 66, 1742 (2001). (Pubitemid 32205112)
16. J. L. Scott, S. R. Parkin, and J. E. Anthony, Synlett, 161 (2004).
17. S. V. Kovalenko, S. Peabody, M. Manoharan, R. J. Clark, and I. V. Alabugin, Org. Lett., 6, 2457 (2004). (Pubitemid 38952562)
18. S. W. Peabody, B. Breiner, S. V. Kovalenko, S. Patil, and I. V. Alabugin, Org. Biomol. Chem., 3, 218 (2005). (Pubitemid 40162741)
19. Q. Zhou, P. J. Carroll, and T. M. Swager, J. Org. Chem., 59, 1294 (1994).
20. P. R. Schreiner, M. Prall, and V. Lutz, Angew. Chem., Int. Ed., 42, 5757 (2003). (Pubitemid 37522571)
21. C.-Y. Lee and M.-J. Wu, Eur. J. Org. Chem., 3463 (2007).
22. A. V. Gulevskaya and A. S. Tyaglivy, Khim. Geterotsikl. Soedin., 87 (2012). [Chem. Heterocycl. Compd., 48, 82 (2012).]
23. M.-J. Wu, C.-F. Lin, and W.-D. Lu, J. Org. Chem., 67, 5907 (2002). (Pubitemid 34912943)
24. H. Li, H.-R. Zhang, J. L. Petersen, and K. K. Wang, J. Org. Chem., 66, 6662 (2001). (Pubitemid 32946583)
25. K. Gilmore and I. V. Alabugin, Chem. Rev., 111, 6513 (2011).
26. B. Godoi, R. F. Schumacher, and G. Zeni, Chem. Rev., 111, 2937 (2011).
27. H. W. Whitlock and P. E. Sandvick, J. Am. Chem. Soc., 88, 4525 (1966).
28. A. V. Gulevskaya, R. Yu. Lazarevich, and A. F. Pozharskii, Tetrahedron, 69, 910 (2013).
29. B. J. Whitlock and H. W. Whitlock, J. Org. Chem., 37, 3559 (1972).
30. D. T. Chase, B. D. Rose, S. P. McClintock, L. N. Zakharov, and M. M. Haley, Angew. Chem., Int. Ed., 50, 1127 (2011).
31. F. Xu, L. Peng, A. Orita, and J. Otera, Org. Lett., 14, 3970 (2012).
32. C. Werner, H. Hopf, J. Grunenberg, and P. G. Jones, Eur. J. Org. Chem., 4027 (2010).
33. I. L. Knunyants and E. Ya. Pervova, Izv. Akad. Nauk SSSR, Ser. Khim., 71 (1967). [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 16, 64 (1967).
34. S. Das and A. Basak, Synlett, 501 (2008).
35. M. Schmittel and S. Kiau, Liebigs Ann. /Recl., 1391 (1997).
36. A. Poloukhtine and V. V. Popik, J. Am. Chem. Soc., 129, 12062 (2007). (Pubitemid 47556820)
37. A. Poloukhtine, V. Rassadin, A. Kuzmin, and V. V. Popik, J. Org. Khim., 75, 5953 (2010).
38. B. Wen, J. L. Petersen, and K. K. Wang, Org. Lett., 13, 168 (2011).
39. R. Liedtke, R. Fröhlich, G. Kehr, and G. Erker, Organometallics, 30, 5222 (2011).
40. T. J. Barton, A. J. Nelson, and J. Clardy, J. Org. Chem., 36, 3995 (1971).
41. J. Blum, Y. Badrieh, O. Shaaya, L. Meltser, and H. Schumann, Phosphorus, Sulfur Silicon, Relat. Elem., 79, 87 (1993).
42. J. Blum, W. Baidossi, Y. Badrieh, R. E. Hoffman, and H. Schumann, J. Org. Chem., 60, 4738 (1995).
43. M. Iyoda, K. Fuchigami, A. Kusaka, T. Yoshida, M. Yoshida, H. Matsuyama, and Y. Kuwatani, Chem. Lett., 860 (2000).
44. Z. Li, J. Hong, L. Weng, and X. Zhou, Tetrahedron, 68, 1552 (2012).
45. C.-C. Chen, S.-C. Yang, and M.-J. Wu, J. Org. Chem., 76, 10269 (2011).
46. K. Hirano, Y. Inaba, K. Takasu, S. Oishi, Y. Takemoto, N. Fujii, and H. Ohno, J. Org. Chem., 76, 9068 (2011).
47. S. Mehta and R. C. Larock, J. Org. Chem., 75, 1652 (2010).
48. A. Odedra, C.-J. Wu, T. B. Pratap, C.-W. Huang, Y.-F. Ran, and R.-S. Liu, J. Am. Chem. Soc., 127, 3406 (2005). (Pubitemid 40372233)