1,4-Pentenyne as a five-carbon synthon for efficient and selective syntheses of natural products containing 2,4-dimethyl-1-penten-1,5-ylidene and related moieties by means of Zr-catalyzed carboalumination of alkynes and alkenes

Chemistry - A European Journal

Volumn 14, Issue 1, 2008, Pages 311-318

  Zhu, Gangguo ^a   Negishi, Ei Ichi ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

Asymmetric synthesis; Catalysis; Natural products; Pentenyne; Zirconium

Indexed keywords

1,4-PENTENYNE; CARBOALUMINATION; FIVE-CARBON SYNTHON; NATURAL PRODUCTS;

CARBON; CATALYSIS; OLEFINS; SYNTHESIS (CHEMICAL); ZIRCONIUM COMPOUNDS;

AROMATIC COMPOUNDS;

ALKENE; ALKYNE; ALUMINUM DERIVATIVE; BIOLOGICAL PRODUCT; CARBON; NAFUREDIN; PYRONE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; ZIRCONIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; SYNTHESIS;

ALKENES; ALKYNES; ALUMINUM COMPOUNDS; BIOLOGICAL PRODUCTS; CARBON; CATALYSIS; LIPASE; MOLECULAR STRUCTURE; PYRONES; ZIRCONIUM;

EID: 38049150096     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701512     Document Type: Article

References (88)

1. a) S. Ômura, H. Miyadera, H. Ui, K. Shiomi, Y. Yamaguchi, R. Masuma, T. Nagamitsu, D. Takano, T. Sunazuka, A. Harder, H. Kölbl, M. Namikoshi, H. Miyoshi, K. Sakamoto, K. Kita, Proc. Natl. Acad. Sci. USA 2001, 98, 60-62;
2. b) D. Takano, T. Nagamitsu, H. Ui, K. Shiomi, Y. Yamaguchi, R. Masuma, I. Kuwajima, S. Ômura, Tetrahedron Lett. 2001, 42, 3017-3020;
3. c) D. Takano, T. Nagamitsu, H. Ui, K. Shiomi, Y. Yamaguchi, R. Masuma, I. Kuwajima, S. Ômura, Org. Lett. 2001, 3, 2289-2291.
4. a) M. Tanaka, F. Nara, K. Suzuki-Konagai, T. Hosoya, T. Ogita, J. Am. Chem. Soc. 1997, 119, 7871-7872;
5. b) S. Saito, N. Tanaka, K. Fujimoto, H. Kogen, Org. Lett. 2000, 2, 505-506;
6. c) Z. Tan, E. Negishi, Angew. Chem. 2004, 116, 2971-2974;
7. Angew. Chem. Int. Ed. 2004, 43, 2911-2914;
8. d) M. Inoue, W. Yokota, M. G. Murugesh, T. Izuhara, T. Katoh, Angew. Chem. 2004, 116, 4303-4305;
9. Angew. Chem. Int. Ed. 2004, 43, 4207-4209;
10. e) R. Takagi, W. Miyanaga, K. Tojo, S. Tsuyumine, K. Ohkata, J. Org. Chem. 2007, 72, 4117-4125.
11. a) D. Schummer, K. Gerth, H. Reichenbach, G. Hoefle, Liebigs Ann. 1995, 685-688;
12. b) M. Christmann, U. Bhatt, M. Quitschalle, E. Claus, M. Kalesse, Angew. Chem. 2000, 112, 4535-4538;
13. Angew. Chem. Int. Ed. 2000, 39, 4364-4366;
14. c) D. R. Williams, D. C. IhIe, S. V. Plummer, Org. Lett. 2001, 3, 1383-1386;
15. d) K. N. Cossey, R. L. Funk, J. Am. Chem. Soc. 2004, 126, 12216-12217.
16. a) H. Mishima, M. Kurabayashi, C. Tamura, S. Sato, H. Kuwano, A. Saito, A. Aoki, Tetrahedron Lett. 1975, 16, 711-714;
17. b) A. B. Smith, III, S. R. Schow, J. D. Bloom, A. S. Thompson, K. N. Winzenberg, J. Am. Chem. Soc. 1982, 104, 4015-4018;
18. c) S. R. Schow, J. D. Bloom, A. S. Thompson, K. N. Winzenberg, A. B. Smith, III, J. Am. Chem. Soc 1986, 108, 2662-2674;
19. d) D. R. Williams, B. A. Barner, K. Nishitani, J. G. Phillips, J. Am. Chem. Soc. 1982, 104, 4708-4710;
20. e) R. Baker, M. J. O'Mahony, C. J. Swain, J. Chem. Soc. Chem. Commun. 1985, 1326-1328;
21. f) S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc. Chem. Commun. 1985, 1386-1388;
22. g) C. Yeates, S. D. A. Stephen, P. Kocienski, S. F. Campbell, J. Chem. Soc. Chem. Commun. 1985, 1388-1389;
23. h) P. J. Kocienski, S. D. A. Street, C. Yeates, S. F. Campbell, J. Chem. Soc. Perkin Trans. 1 1987, 2171-2181;
24. i) S. V. Attwood, A. G. M. Barrett, R. A. E. Carr, G. Richardson, J. Chem. Soc. Chem. Commun. 1986, 479-481;
25. j) M. Li, G. A. O'Doherty, Org. Lett. 2006, 8, 3987-3990.
26. a) A. Takle, P. Kocienski, Tetrahedron Lett. 1989, 30, 1675-1678;
27. b) A. Takle, P. Kocienski, Tetrahedron 1990, 46, 4503-4516.
28. a) D. A. Evans, M. A. Calter, Tetrahedron Lett. 1993, 34, 6871-6874;
29. b) K. Toshima, T. Jyojima. H. Yamaguchi, H. Murase, T. Yoshida, S. Matsumura, M. Nakata, Tetrahedron Lett. 1996, 37, 1069-1072;
30. c) K. Toshima. H. Yamaguchi, T. Jyojima, Y. Noguchi, M. Nakata, S. Matsumura. Tetrahedron Lett. 1996, 37, 1073-1076;
31. d) K. Toshima, T. Jyojima, H. Yamaguchi, Y. Noguchi, T. Yoshida, H. Murase, M. Nakata, S. Matsumura, J. Org. Chem. 1997, 62, 3271-3284;
32. e) K. A. Scheidt, A. Tasaka, T. D. Bannister, M. D. Wendt, W. R. Roush, Angew. Chem. 1999, 111, 1760-1762;
33. Angew. Chem. Int. Ed. 1999, 38, 1652-1655;
34. f) K. A. Scheidt, T. D. Bannister, A. Tasaka, M. D. Wendt, B. M. Savall, G. J. Fegley, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 6981-6990;
35. g) J. A. Marshall, N. D. Adams, Org. Lett. 2000, 2, 2897-2900;
36. h) J. A. Marshall, N. D Adams, J. Org. Chem. 2002, 67, 733-740;
37. i) S. Hanessian, J. Ma, W. Wang, J. Am. Chem. Soc. 2001, 123, 10200-10206;
38. j) J.-C. Poupon, E. Demont, J. Prunet, J.-P. Férézou, J. Org. Chem. 2003, 68, 4700-4707.
39. a) T. Jyojima, N. Miyamoto, M. Katohno, M. Nakata, S. Matsumura, K. Toshima, Tetrahedron Lett. 1998, 39, 6007-6010;
40. b) K. Toshima, T. Jyojima, N. Miyamoto, M. Katohno, M. Nakata, S. Matsumura, J. Org. Chem. 2001, 66, 1708-1715;
41. c) I. Paterson, V. A. Doughty, M. D. McLeod, T. Trieselmann, Angew. Chem. 2000, 112, 1364-1368;
42. Angew. Chem. Int. Ed. 2000, 39, 1308-1312.
43. a) T. K. Jones, S. G. Mills, R. A. Reamer, D. Askin, R. Desmond, R. P. Volante, I. Shinkai, J. Am. Chem. Soc. 1989, 111, 1157-1159;
44. b) R. E. Ireland, P. Wipf, Tetrahedron Lett. 1989, 30, 919-922;
45. c) T. K. Jones. R. A. Reamer. R. Desmond, S. G. Mills, J. Am. Chem. Soc. 1990, 112, 2998-3017;
46. d) M. Nakatsuka, J. A. Ragan, T. Sammakia, D. B. Smith, D. E. Uehling, S. L. Schreiber, J. Am. Chem. Soc. 1990, 112, 5583-5601;
47. e) R. E. Ireland, J. L. Gleason, L. D. Gegnas, T. K. Highsmith, J. Org. Chem. 1996, 61, 6856-6872;
48. f) R. E. Ireland, L. Liu, T. D. Roper, Tetrahedron 1997, 53, 13221-13256.
49. a) A. B. Smith, III, Y. Qiu, D. R. Jones, K. Kobayashi, J. Am. Chem. Soc. 1995, 117, 12011-12012;
50. b) S. S. Harried, G. Yang, M. A. Strawn, D. C. Myles, J. Org. Chem. 1997, 62, 6098-6099;
51. c) J. A. Marshall, B. A. Johns, J. Org. Chem. 1998, 63, 7885-7892;
52. d) I. Paterson, G. J. Florence, K. Gerlach, J. Scott, Angew. Chem. 2000, 112, 385-388;
53. Angew. Chem. Int. Ed. 2000, 39, 377-380.
54. a) N. Murakami, W. Wang, M. Aoki, Y. Tsutsui, M. Sugimoto, M. Kobayashi, Tetrahedron Lett. 1998, 39, 2349-2352;
55. b) A. B. Smith, III, B. M. Brandt, Org. Lett. 2001, 3, 1685-1688;
56. c) M. Kalesse, M. Quitschalle, C. P. Khandavalli, A. Saeed, Org. Lett. 2001, 3, 3107-3109;
57. d) J. A. Marshall, M. P. Bourbeau, J. Org. Chem. 2002, 67, 2751-2754;
58. e) M. Lautens, T. A. Stammers, Synthesis 2002, 1993-2012;
59. f) N. F. Langille, J. S. Panek, Org. Lett. 2004, 6, 3203-3206.
60. I. R. Corre̊a, Jr., R. A. Pilli, Angew. Chem. 2003, 115, 3125-3128;
61. Angew. Chem. Int. Ed. 2003, 42, 3017-3020.
62. C. Roberts, J. C. Walton, J. Chem. Soc. Perkin Trans. 2 1981, 553-559.
63. M. Qian, E. Negishi, Synlett 2005, 1789-1793.
64. a) D. E. Van Horn, E. Negishi, J. Am. Chem. Soc. 1978, 100, 2254-2256;
65. b) C. L. Rand, D. E. Van Horn, M. W. Moore, E. Negishi, J. Org. Chem. 1981, 46, 4093-4096;
66. c) E. Negishi, D. E. Van Horn, T. Yoshida, J. Am. Chem. Soc. 1985, 107, 6639-6647;
67. d) G. Wang, G, Zhu, E. Negishi, J. Organomet. Chem. 2007, 692, 4731-4736.
68. a) D. Kondakov, E. Negishi, J. Am. Chem. Soc. 1995, 117, 10771-10772;
69. b) D. Kondakov, E. Negishi, J. Am. Chem. Soc. 1996, 118, 1577-1578;
70. c) S. Huo, E. Negishi, Org. Lett. 2001, 3, 3253-3256;
71. d) E. Negishi, Z. Tan, B. Liang, T. Novak, Proc. Natl. Acad. Sci. USA 2004, 101, 5782-5787;
72. e) T. Novak, Z. Tan, B. Liang, E. Negishi, J. Am. Chem. Soc. 2005, 127, 2838-2839;
73. f) B. Liang, T. Novak, Z. Tan, E. Negishi, J. Am. Chem. Soc. 2006, 128, 2770-2771;
74. g) Z. Tan, B. Liang, S. Huo, J. Shi, E. Negishi, Tetrahedron: Asymmetry 2006, 17, 512-515;
75. h) G. Zhu, E. Negishi, Org. Lett. 2007, 9, 2771-2774.
76. Z. Huang, Z. Tan, T. Novak, G. Zhu, E. Negishi, Adv. Synth. Catal. 2007, 349, 539-545.
77. a) E. Negishi, N. Okukado, A. O. King, D. E. Van Horn, B. I. Spiegel, J. Am. Chem. Soc. 1978, 100, 2254-2256;
78. b) E. Negishi, Z. Owczarczyk, Tetrahedron Lett. 1991, 32, 6683-6686;
79. c) F. Zeng, E. Negishi, Org. Lett. 2001, 3, 719-722;
80. d) N. Yin, G. Wang, M. Qian, E. Negishi, Angew. Chem. 2006, 118, 2982-2986;
81. Angew. Chem. Int. Ed. 2006, 45, 2916-2920.
82. G. Erker, M. Aulbach, M. Knickmeier, D. Wingbermuhle, C. Kruger, M. Nolte, S. Werner, J. Am. Chem. Soc. 1993, 115, 4590-4601.
83. D. L. Comins, J. D. Brown, J. Org. Chem. 1984, 49, 1078-1083.
84. a) A. O. King, N. Okukado, E. Negishi, J. Chem. Soc. Chem. Commun. 1977, 683-684;
85. b) A. O. King, E. Negishi, F. J. Villani, Jr., A. Silverira, Jr., J. Org. Chem. 1978, 43, 358-360;
86. c) E. Negishi, M. Kotora, C. Xu, J. Org. Chem. 1997, 62, 8957-8960.
87. P. Wipf, S. Ribe, Org. Lett. 2000, 2, 1713-1716.
88. H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 293-294.