Rhodium-catalyzed tandem heterocyclization and carbonylative [(3+2)+1] cyclization of diyne-enones

Organic Letters

Volumn 13, Issue 4, 2011, Pages 688-691

  Zhao, Wanxiang ^a   Zhang, Junliang ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79951629063     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102920f     Document Type: Article

References (75)

1. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635
2. Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901
3. Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813
4. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127
5. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
6. Wender, P. A.; Gamber, G. G.; Williams, T. J. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; Chapter 13, p 263 and references cited therein.
7. Klunder, A. J. H.; Zhu, J.; Zwanenburg, B. Chem. Rev. 1999, 99, 1163
8. Ho, T.-L. Enantioselective Synthesis: Natural Products Synthesis from Chiral Terpenes; Wiley: New York, 1992.
9. Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650
10. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668
11. Mohr, P. J.; Halcomb, R. L. J. Am. Chem. Soc. 2003, 125, 1712
12. Furuya, S.; Terashima, S. Tetrahedron Lett. 2003, 44, 6875
13. Taber, D. F.; Storck, P. H. J. Org. Chem. 2003, 68, 7768
14. Booker-Milbum, K. I.; Jenkins, H.; Charmant, J. P. H.; Mohr, P. Org. Lett. 2003, 5, 3309
15. Goeke, A.; Mertl, D.; Brunner, G. Angew. Chem., Int. Ed. 2005, 44, 99
16. Lakshmi, R.; Bateman, T. D.; McIntosh, M. C. J. Org. Chem. 2005, 70, 5313
17. Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779
18. Wilson, E. M.; Trauner, D. Org. Lett. 2007, 9, 1327
19. Wessig, P.; Müller, G. Chem. Rev. 2008, 108, 2051
20. Reymond, S.; Cossy, J. Chem. Rev. 2008, 108, 5359
21. Pellissier, H. Tetrahedron 2009, 65, 2839
22. Juhl, M.; Tanner, D. Chem. Soc. Rev. 2009, 38, 2983
23. Franck, G.; Brödner, K.; Helmchen, G. Org. Lett. 2010, 12, 3886
24. For recent examples, see: Evans, P. A.; Sawyer, J. R.; Inglesby, P. A. Angew. Chem., Int. Ed. 2010, 122, 5746
25. Qiu, Z.; Wang, S. R.; Xie, Z. Angew. Chem., Int. Ed. 2010, 122, 4649
26. Miura, T.; Morimoto, M.; Murakami, M. J. Am. Chem. Soc. 2010, 132, 15836
27. Ogoshi, S.; Nishimura, A.; Ohashi, M. Org. Lett. 2010, 12, 3450
28. Yoshikai, N.; Zhang, S.-L.; Yamagata, K.; Tsuji, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 4099
29. Friedman, R. K.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 10775
30. Dalton, D. M.; Oberg, K. M.; Yu, R. T.; Lee, E. E.; Perreault, S.; Oinen, M. E.; Pease, M. L.; Malik, G.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 15717
31. For recent reviews, see: Fujiwara, M.; Ojima, I. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; Chapter 7, p 129 and references cited therein.
32. Robinson, J. E. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; Chapter 12, p 241 and references cited therein.
33. Inglesby, P. A.; Evans, P. A. Chem. Soc. Rev. 2010, 39, 2791
34. Leboeuf, D.; Gandon, V.; Malacria, M. In Handbook of Cyclization Reactions; Ma, S., Ed.; Wiley-VCH: Weinheim, 2010; Chapter 8, p 367 and references cited therein.
35. For examples of transition-metal-catalyzed [5+1] cyclization reactions, see: Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4
36. Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230
37. Kurahashi, T.; de Meijere, A. Synlett 2005, 2619
38. Odedra, A.; Wu, C.-J.; Madhushaw, R. J.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 9610
39. Brancour, C.; Fukuyama, T.; Ohta, Y.; Ryu, I.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Chem. Commun. 2010, 5470
40. Lee, S. I.; Park, J. H.; Chung, Y. K.; Lee, S.-G. J. Am. Chem. Soc. 2004, 126, 2714
41. Jiao, L.; Lin, M.; Zhuo, L.-G.; Yu, Z.-X. Org. Lett. 2010, 12, 2528
42. Li, C.; Zhang, H.; Feng, J.; Zhang, Y.; Wang, J. Org. Lett. 2010, 12, 3082
43. Jiao, L.; Yuan, C.; Yu, Z.-X. J. Am. Chem. Soc. 2008, 130, 4421
44. Wang, Y.; Wang, J.; Su, J.; Huang, F.; Jiao, L.; Liang, Y.; Yang, D.; Zhang, S.; Wender, P. A.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 10060
45. For ruthenium-catalyzed [3+2+1] cyclization, see: Fukuyama, T.; Higashibeppu, Y.; Yamaura, R.; Ryu, I. Org. Lett. 2007, 9, 587
46. Zhao, W.; Zhang, J. Chem. Commum. 2010, 46, 7816
47. For selected examples of oxidative ring opening of furan, see: Lepage, L.; Lepage, Y. Synthesis 1983, 1018
48. O'brien, B. A.; Lam, W. Y.; DesMarteau, D. D. J. Org. Chem. 1986, 51, 4466
49. Manfredi, K. P.; Jennings, P. W. J. Org. Chem. 1989, 54, 5186
50. Wahlen, J.; Moens, B.; De Vos, D. E.; Alsters, P. L.; Jacobsa, P. A. Adv. Synth. Catal. 2004, 346, 333
51. Pearlman, B. A.; Padilla, A. G.; Hach, J. T.; Havens, J. L.; Pillai, M. D. Org. Lett. 2006, 8, 2111
52. Tokumaru, K.; Arai, S.; Nishida, A. Org. Lett. 2006, 8, 27
53. Margaros, I.; Vassilikogiannakis, G. J. Org. Chem. 2008, 73, 2021
54. Montagnon, T.; Tofi, M.; Vassilikogiannakis, G. Acc. Chem. Res. 2008, 41, 1001
55. Tofi, M.; Koltsida, K.; Vassilikogiannakis, G. Org. Lett. 2009, 11, 313
56. Pavlakos, E.; Georgiou, T.; Tofi, M.; Montagnon, T.; Vassilikogiannakis, G. Org. Lett. 2009, 11, 4556
57. Hanson, J. R. Nat. Prod. Rep. 1995, 12, 381
58. Blight, M. M.; Grove, J. F. J. Chem. Soc., Perkin Trans. 1 1986, 1317
59. Pecher, T. J.; Weber, H.-P.; Kis, S. J. Chem. Soc., Chem. Commun. 1972, 1061
60. Carlini, R.; Higgs, K.; Older, C.; Randhawa, S. J. Org. Chem. 1997, 62, 2330
61. Souza, F. E. S.; Rodrigo, R. Chem. Commun. 1999, 1947
62. Wymann, M. P.; Bulgarelli-Leva, G.; Zvelebil, M. J.; Pirola, L.; Vanhaesebroeck, B.; Waterfield, M. D.; Panayotou, G. Mol. Cell. Biol. 1996, 16, 1722
63. Walker, E. H.; Pacold, M. E.; Perisic, O.; Stephens, L.; Hawkins, P. T.; Wymann, M. P.; Williams, R. L. Mol. Cell 2000, 6, 909
64. Arcaro, A.; Wymann, M. P. Biochem. J. 1993, 296, 297
65. Okada, T.; Sakuma, L.; Fukui, Y.; Hazeki, O.; Ui, M. J. Biol. Chem. 1994, 269, 3563
66. Cross, M. J.; Stewart, A.; Hodgkin, M. N.; Kerr, D. J.; Wakelam, M. J. O. J. Biol. Chem. 1995, 270, 25352
67. Tyman, J. H. P. Synthetic and Natural Phenols; Elsevier: New York, 1996.
68. Ferruginol; Ohashi, M.; Maruishi, T.; Kakisama, H. Tetrahedron Lett. 1968, 719
69. Hinokiol; Matsumoto, T.; Usui, S.; Kamashima, H. Bull. Chem. Soc. Jpn. 1981, 54, 581
70. Jacobi, P. A.; Kravitz, J. I.; Zheng, W. J. Org. Chem. 1995, 60, 376
71. Rappoport, Z. The Chemistry of Phenols; Wiley-VCH: Weinheim, 2003.
72. Gao, K.; Jia, Z. Phytochemistry 1998, 49, 38 and references cited therein
73. Fukumoto, S.; Shiraishi, M.; Terashita, Z.-i.; Ashida, Y.; Inada, Y. J. Med. Chem. 1992, 35, 2202
74. Attempted isolation of the compounds 2b and 2k resulted in either decomposition or further oxidation.
75. CCDC 795202 (2h) and 795203 (3a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ datarequest/cif.