Expeditious cascade reactions: Controlled syntheses of fenestradienes and cyclooctatrienes under palladium catalysis

Tetrahedron

Volumn 69, Issue 36, 2013, Pages 7568-7591

  Charpenay, Mélanie ^a,b   Boudhar, Aicha ^a,c   Hulot, Catherine ^a   Blond, Gaëlle ^a   Suffert, Jean ^a  

^a Faculté de Pharmacie   (France)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

4 exo Dig; Cascade; Cyclooctatrienes; Fenestradienes; Palladium

Indexed keywords

PALLADIUM;

ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CYCLIZATION; DIASTEREOISOMER; HYDROGENATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; ROOM TEMPERATURE; SONOGASHIRA REACTION; STEREOCHEMISTRY;

EID: 84880923507     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.05.089     Document Type: Article

References (84)

1. L.F. Tietze, and U. Beifuss Angew. Chem; Int. Ed. Engl. 32 1993 131
2. A. De Meijere, and F.E. Meyer Angew. Chem; Int. Ed. Engl. 33 1994 2379
3. A. Heumann, and M. Réglier Tetrahedron 52 1996 9289
4. M. Malacria Chem. Rev. 96 1996 289
5. E. Negishi, C. Copéret, S. Ma, S.-Y. Liou, and F. Liu Chem. Rev. 96 1996 365
6. A. De Meijere, and S. Bräse J. Organomet. Chem. 576 1999 88
7. R. Grigg, and V. Sridharan J. Organomet. Chem. 576 1999 65
8. G. Poli, G. Giambastiani, and A. Heumann Tetrahedron 56 2000 5959
9. L.F. Tietze, H. Ila, and H.P. Bell Chem. Rev. 104 2004 3453
10. K.C. Nicolaou, D.J. Edmonds, and P.G. Bulger Angew. Chem; Int. Ed. 45 2006 7134
11. Y. Yamamoto Chem. Rev. 112 2012 4736
12. B.M. Trost Science 254 1991 1471
13. B.M. Trost Angew. Chem; Int. Ed. Engl. 34 1995 259
14. P.A. Wender, S.T. Handy, and D.L. Wright Chem. Ind. 1997
15. R.A. Sheldon Pure Appl. Chem. 72 2000
16. P.A. Wender, and B.L. Miller Nature 460 2009
17. U. Lauer, T. Anke, W.S. Sheldrick, A. Scherer, and W. Steglich J. Antibiot. 42 1989 875
18. F. Sugawara, N. Takahashi, G. Strobel, C.H. Yun, G. George, Y. Fu, and J. Clardy J. Org. Chem. 53 1988 2170
19. T.K. Au, W.S.H. Chick, and P.C. Leung Life Sci. 67 2000 733
20. J.R. Hanson Nat. Prod. Rep. 3 1986 123
21. J.R. Hanson Nat. Prod. Rep. 9 1992 481
22. X. Shen, S.B. Krasnoff, S.W. Lu, C.D. Dunbar, J. O'Neal, B.G. Turgeon, O.C. Yoder, D.M. Gibson, and M.T. Hamann J. Nat. Prod. 62 1999 895
23. S. Nozoe, M. Morisaki, K. Tsuda, Y. Iitaka, N. Takahashi, S. Tamura, K. Ishibashi, and M. Shirasaka J. Am. Chem. Soc. 87 1965 4968
24. E. Li, A.M. Clark, and C.D. Hufford J. Nat. Prod. 58 1995 57
25. M.C. Wani, H.L. Taylor, M.E. Wall, P. Coggon, and A.T. McPhail J. Am. Chem. Soc. 93 1971 2325
26. R.M. Coates, J.W. Muskopf, and P.A. Senter J. Org. Chem. 50 1985 3541
27. M. Rowley, M. Tsukamoto, and Y. Kishi J. Am. Chem. Soc. 111 1989 2735
28. L.A. Paquette, S. Liang, and P. Galatsis Synlett 1990 663
29. B.B. Snider, and K. Yang J. Org. Chem. 57 1992 3615
30. P.A. Wender, J.M. Nuss, D.B. Smith, A. Suarez-Sobrino, J. Vagberg, D. Decosta, and J. Bordner J. Org. Chem. 62 1997 4908
31. P.C.K. Lo, and M.L. Snapper Org. Lett. 3 2001 2819
32. P.K. Ruprah, J.-P. Cros, J.E. Pease, W.G. Whittingham, and J.M.J. Williams Eur. J. Org. Chem. 2002 2002 3145
33. Y. Oonishi, A. Hosotani, and Y. Sato Angew. Chem; Int. Ed. 51 2012 11548
34. S.A. Snyder, A.P. Brucks, D.S. Treitler, and I. Moga J. Am. Chem. Soc. 134 2012 17714
35. B. Salem, and J. Suffert Angew. Chem; Int. Ed. 43 2004 2826
36. C. Bour, G. Blond, B. Salem, and J. Suffert Tetrahedron 62 2006 10567
37. A.C. Cope, A.C. Haven, F.L. Ramp, and E.R. Trumbull J. Am. Chem. Soc. 74 1952 4867
38. R. Huisgen, G. Boche, A. Dahmen, and W. Hechtl Tetrahedron Lett. 9 1968 5215
39. A.J. Fry Tetrahedron 64 2008 2101
40. For references on endiandric acids syntheses, see K.C. Nicolaou, N.A. Petasis, J. Uenishi, and R.E. Zipkin J. Am. Chem. Soc. 104 1982 5557
41. K.C. Nicolaou, N.A. Petasis, and R.E. Zipkin J. Am. Chem. Soc. 104 1982 5560
42. K.C. Nicolaou, N.A. Petasis, R.E. Zipkin, and J. Uenishi J. Am. Chem. Soc. 104 1982 5555
43. K.C. Nicolaou, R.E. Zipkin, and N.A. Petasis J. Am. Chem. Soc. 104 1982 5558
44. For references on SNF4435C and D syntheses, see K. Kurosawa, K. Takahashi, and E. Tsuda J. Antibiot. 54 2001 541
45. K. Takahashi, E. Tsuda, and K. Kurosawa J. Antibiot. 54 2001 548
46. C.M. Beaudry, and D. Trauner Org. Lett. 4 2002 2221
47. K. Kurosawa, K. Takahashi, N. Fujise, Y. Yamashita, N. Washida, and E. Tsuda J. Antibiot. 55 2002 71
48. J.E. Moses, J.E. Baldwin, R. Marquez, R.M. Adlington, and A.R. Cowley Org. Lett. 4 2002 3731
49. K.A. Parker, and Y.H. Lim J. Am. Chem. Soc. 126 2004 15968
50. J.E. Barbarow, A.K. Miller, and D. Trauner Org. Lett. 7 2005 2901
51. C.M. Beaudry, and D. Trauner Org. Lett. 7 2005 4475
52. M.F. Jacobsen, J.E. Moses, R.M. Adlington, and J.E. Baldwin Org. Lett. 7 2005 2473
53. For references on ocellapyrones syntheses, see E. Manzo, M.L. Ciavatta, M. Gavagnin, E. Mollo, S. Wahidulla, and G. Cimino Tetrahedron Lett. 46 2005 465
54. A.K. Miller, and D. Trauner Angew. Chem; Int. Ed. 44 2005 4602
55. J.E. Moses, R.M. Adlington, R. Rodriguez, S.J. Eade, and J.E. Baldwin Chem. Commun. 2005 1687
56. For references on elysiapyrones syntheses, see J.E. Barbarow, A.K. Miller, and D. Trauner Org. Lett. 7 2005 2901
57. M. Cueto, L. D'Croz, J.L. Mate, A. San-Martin, and J. Darias Org. Lett. 7 2005 415
58. J.J. Beck, G.B. Merrril, J.D. Palumbo, and T.L. O'Keffe J. Agric. Food Chem. 56 2008 11382
59. C.M. Beaudry, J.P. Malerich, and D. Trauner Chem. Rev. 105 2005 4757
60. R.E. Corbett, C.M. Couldwell, D.R. Lauren, and R.T. Weavers J. Chem. Soc; Perkin Trans. 1 1979 1791
61. R.E. Corbett, D.R. Lauren, and R.T. Weavers J. Chem. Soc; Perkin Trans. 1 1979 1774
62. R.E. Corbett, J.R. Guild, D.R. Lauren, and R.T. Weavers Aust. J. Chem. 44 1991 1139
63. S.H. Shim, J.B. Gloer, and D.T. Wicklow J. Nat. Prod. 69 2006 1601
64. S.H. Shim, D.C. Swenson, J.B. Gloer, P.F. Dowd, and D.T. Wicklow Org. Lett. 8 2006 1225
65. T. Gaich, and J. Mulzer J. Am. Chem. Soc. 131 2009 452
66. T. Gaich, and J. Mulzer Org. Lett. 12 2010 272
67. N. Ingavat, C. Mahidol, S. Ruchirawat, and P. Kittakoop J. Nat. Prod. 74 2011 1650
68. G. Mehta, and T.B. Khan Tetrahedron Lett. 53 2012 4558
69. B.R. Venepalli, and W.C. Agosta Chem. Rev. 87 1987 399
70. R. Keese Chem. Rev. 106 2006 4787
71. C. Hulot, G. Blond, and J. Suffert J. Am. Chem. Soc. 130 2008 5046
72. C. Hulot, S. Amiri, G. Blond, P. Schreiner, and J. Suffert J. Am. Chem. Soc. 131 2009 13387
73. G. Blond, C. Bour, B. Salem, and J. Suffert Org. Lett. 10 2008 1075
74. M. Charpenay, A. Boudhar, A. Siby, S. Schigand, G. Blond, and J. Suffert Adv. Synth. Catal. 353 2011 3151
75. M. Charpenay, A. Boudhar, G. Blond, and J. Suffert Angew. Chem; Int. Ed. 51 2012 4379
76. M. Ghandi, A.-T. Ghomi, and M. Kubicki J. Org. Chem. 2013 10.1021/jo302790y
77. V. Gevorgyan, and M. Rubina J. Am. Chem. Soc. 123 2001 11107
78. B.M. Trost, M.T. Sorum, C. Chan, A.E. Harms, and G. Ruhter J. Am. Chem. Soc. 119 1997 698
79. N. Tsukada, S. Ninomiya, Y. Aoyama, and Y. Inoue Org. Lett. 9 2007 2919
80. B. Lecea, A. Arrieta, and F.P. Cossio J. Org. Chem. 70 2005 1035
81. M. Hesse, H. Meier, and B. Zeeh Spectroscopic Methods in Organic Chemistry 2007 Thieme
82. F. Lehrich, H. Hopf, and J. Grunenberg Eur. J. Org. Chem. 2011 2705
83. H. Yang, Y. Li, M. Jiang, J. Wang, and H. Fu Chem. - Eur. J. 17 2011 5652
84. C. Morril, and R.H. Grubbs J. Org. Chem. 68 2003 6031