Formal total synthesis of oximidine II via a Suzuki-type cross-coupling macrocyclization employing potassium organotrifluoroborates

Journal of the American Chemical Society

Volumn 126, Issue 33, 2004, Pages 10313-10318

  Molander, Gary A ^a   Dehmel, Florian ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; COUPLED CIRCUITS; STABILITY; SYNTHESIS (CHEMICAL);

HYDROBORATING REAGENT; MACROLACTONE; OXIMIDINE;

POTASSIUM COMPOUNDS;

ALCOHOL DERIVATIVE; ALDEHYDE; IMIDE; LACTONE; ORGANOBORON DERIVATIVE; OXIMIDINE II; OXYGEN; POTASSIUM; REAGENT; SNIECKUS REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CARREIRA PROTOCOL; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; MACROCYCLIZATION; MACROMOLECULE; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS; TECHNIQUE;

ALKENES; BORATES; CYCLIZATION; HYDROCARBONS, FLUORINATED; LACTONES; STEREOISOMERISM;

EID: 4143060313     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047190o     Document Type: Article

References (90)

1. (a) Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Org. Chem. 1999, 64, 153-155.
2. (b) Hayakawa, Y.; Tomikawa, T.; Shin-Ya, K.; Arao, N.; Nagai, K.; Suzuki, H.-I.; Furihata, K. J. Antibiot. 2003, 56, 905-908.
3. (c) Galinis, D. L.; McKee, T. C.; Pannell, L. K.; Cardellina, J. H., II.; Boyd, M. R. J. Org. Chem. 1997, 62, 8968-8969.
4. (d) McKee, T. C.; Galinis, D. L.; Pannell, L. K.; Cardellina, J. H., II.; Laakso, J.; Ireland, C. M.; Murray, L.; Capon, R. J.; Boyd, M. R. J. Org. Chem. 1998, 63, 7805-7810.
5. (e) Suzumura, K.-i.; Takahashi, I.; Matsumoto, H.; Nagai, K.; Setiawan, B.; Rantiatmodjo, R. M.; Suzuki, K.-i.; Nagano, N. Tetrahedron Lett. 1997, 38, 7573-76.
6. (f) Dekker: K. A.; Aiello, R. J.; Hirai, H.; Inagaki, T.; Sakakibara, T.; Suzuki, Y.; Thompson, J. F.; Yamauchi, Y.; Kojima, N. J. Antibiot. 1998, 51, 14-20.
7. (g) Jansen, R.; Kunze, B.; Reichenbach, H.; Höfle, G. Eur. J. Org. Chem. 2000, 913-919.
8. (h) Kunze, B.; Jansen, R.; Sasse, F.; Höfle, G.; Reichenbach, H. J. Antibiot. 1998, 51, 1075-1080.
9. (i) Erickson, K. L.; Beutler, J. A.; Cardellina, J. H., II.; Boyd, M. R. J. Org. Chem. 1997, 62, 8188-8192.
10. (a) Boyd, M. R.; Farina, C.; Befiore P.; Gagliardi, S.; Kim, J. W.; Hayakawa, Y.; Beutler, J. A.; McKee, T. C.; Bowman, B. J.; Bowman, E. J. J. Pharmacol. Exp. Ther. 2001, 297, 114-120.
11. (b) Beutler, J. A.; McKee, T. C. Curr. Med. Chem. 2003, 10, 787-796.
12. (a) Yadav, J. S.; Srihari, P. Tetrahedron: Asymmetry 2004, 15, 81-89.
13. (b) Herb, C.; Maier, M. E. J. Org. Chem. 2003, 68, 8129-813.
14. (c) Yang, K. L.; Blackman, B.; Diederich, W.; Flaherty, P. T.; Mossman, C. J.; Roy, S.; Ahn, Y. M.; Georg, G. I. J. Org. Chem. 2003, 68, 10030-10039.
15. (d) Yang, K. L.; Haack, T.; Blackman, B.; Diederich, W. E.; Srinivas Pusuluri, S. R.; Georg, G. I. Org. Lett. 2003, 5, 4007-4009.
16. (e) Smith, A. B., III.; Zheng, J. Y. Tetrahedron 2002, 58, 6455-6471.
17. (f) Wu, Y. S.; Liao, X. B.; Wang, R. F.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245-3253.
18. (g) Fürstner, A.; Dierkes, T.; Thiel, O. R.; Blanda, G. Chem. Eur. J. 2001, 7, 5286-5298.
19. (h) Smith, A. B., III.; Zheng, J. Y. Synlett 2001, 1019-1023.
20. (i) Snider, B. B.; Song, F. B. Org. Lett. 2001, 3, 1817-1820.
21. (j) Wu, Y. S.; Esser, L.; De Brabander, J. K. Angew. Chem. Int. Ed. 2000, 39, 4308-4310.
22. (k) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645-2648.
23. (a) Bauer, M.; Maier, M. E. Org. Lett. 2002, 4, 2205-2208.
24. (b) Holloway, G. A.; Hügel, H. M.; Rizzacasa, M. A. J. Org. Chem. 2003, 68, 2200-2204.
25. (a) Graetz, B. R.; Rychnovsky, S. D. Org. Lett. 2003, 5, 3357-3360.
26. (b) Su, Q. B.; Panek, J. S. J. Am. Chem. Soc. 2004, 126, 2425-2430.
27. (c) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Org. Biomol. Chem. 2003, 1, 104.
28. (d) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2001, 42, 5549-5552.
29. (e) Nicolaou, K. C.; Kim, D. W.; Baati, R. K.; O'Brate, A.; Giannakakou, P. Chem. Eur. J. 2003, 9, 6177-6191.
30. (f) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem., Int. Ed. 2002, 41, 3701-3704.
31. (g) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220.
32. (h) Shen, R. C.; Lin, C. T.; Bowman, E. J.; Bowman, B. J.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 7889-7901.
33. (i) Shen, R. C.; Lin, C. T.; Porco, J. A., Jr. J. Am. Chem. Soc. 2002, 124, 5650-5651.
34. (j) Hilli, F.; White, J. M.; Rizzacasa, M. A. Org. Lett. 2004, 6, 1289-1292.
35. (k) Kühnert, S.; Maier, M. E. Org. Lett. 2002, 4, 643-646.
36. Wang, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 6040-6041.
37. Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336.
38. (a) Haack, T.; Kutkaya, S.; Snyder, J. P.; Georg, G. I. Org. Lett. 2003, 5, 5019-5022.
39. (b) Coleman, R. S.; Garg, R. Org. Lett. 2001, 3, 3487-3490.
40. (c) Harvey, J. E.; Raw, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2003, 44, 7209-7212.
41. (d) Scheufler, F.; Maier, M. E. Synlett 2001, 1221-1224.
42. Yet, L. Chem. Rev. 2003, 103, 4283-4306.
43. (a) Molander, G. A.; Rivero, M. R. Org. Lett. 2002, 4, 107-109.
44. (b) Molander, G. A.; Bernardi, C. J. Org. Chem. 2002, 67, 8424-8429.
45. (c) Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313-4327.
46. (a) Porco, J. A., Jr.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410-7411.
47. (b) Lu, Y.-F.; Harwig, C. W.; Fallis, A. G. J. Org. Chem. 1993, 58, 4202-4204.
48. (c) Lu, Y.-F.; Harwig, C. W.; Fallis, A. G. Can. J. Chem. 1995, 73, 2253-2262.
49. (a) Brown, H. C.; Blue, C. D.; Nelson, D. J.; Bhat, N. G. J. Org. Chem. 1989, 54, 6064-6067.
50. (b) Hoshi, M.; Arase, A. Synth. Commun. 1997, 27, 567-572.
51. (c) Zweifel, G.; Arzoumanian, H. J. J. Am. Chem. Soc. 1967, 89, 5086-5088.
52. (a) Isobe, M.; Ichikawa, Y.; Bai, D.-I.; Goto, T. Tetrahedron Lett. 1985, 26, 5203-5206.
53. (b) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 5, 2896-2901.
54. (c) Herradon, B. Tetrahedron: Asymmetry 1991, 2, 191-194.
55. (d) Guo, Z.; Padmakumar, R.; Hollingsworth, R. I.; Radhakrishnan, K. V.; Nandakumar, M. V.; Fraser-Reid, B. Synlett 2003, 7, 1067-1069.
56. (e) Flögel, O.; Amombo, M. G. O.; Reissig, H.-U.; Zahn, G.; Brüdgam, I.; Hartl, H. Chem. Eur. J. 2003, 9, 1405-1415.
57. (a) Boyall, D.; Frantz, D. E.; Carreira, E. M. Org. Lett. 2002, 4, 2605-2606.
58. (b) El-Sayed, E.; Anand, N. K.; Carreira, E. M. Org. Lett. 2001, 3, 3017-3020.
59. (c) Boyall, D.; López, F.; Sasaki, H.; Frantz, D. E.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236.
60. (d) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807.
61. (e) Frantz, D. E.; Fässler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373381.
62. (f) Maezaki, N.; Kojima, N.; Tominaga, H.; Yanai, M.; Tanaka, T. Org. Lett. 2003, 5, 1411-1414.
63. (a) Schmidt, H. M.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1967, 86, 1138-1142.
64. (b) Corey, E. J.; Ritter, K.; Yus, M.; Najera, C. Tetrahedron Lett. 1987, 28, 3547-3550.
65. (c) Gueugnot, S.; Alami, M.; Linstrumelle, G.; Mambu, L.; Petit, Y.; Larcheveque, M.; Tetrahedron 1996, 52, 6635-6646.
66. (d) Hansen, T. V.; Stenstroem, Y. Tetrahedron: Asymmetry 2001, 12, 1407-1409.
67. (e) Marquez, M. D. de; Thaller, V. J. Chem. Res. Miniprint 1985, 4, 1268.
68. (f) Nicolaou, K. C.; Ladduwahetty, T.; Elisseou, E. M. J. Chem. Soc. Chem. Commun. 1985, 1580-1581.
69. For DIBALH deprotection on similar systems, see: (a) Mikami, T.; Asano, H.; Mitsunobu, O. Chem. Lett. 1987, 2033-3036.
70. (b) Sulikowski, G. A.; Lee, W.-M.; Jin, B.; Wu B. Org. Lett. 2000, 2, 1439-1442.
71. See also: (a) Fürstner, A.; Konetzki, I. J. Org. Chem. 1998, 63, 3072-3080.
72. (b) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220.
73. (a) de Lera, A. R.; Torrado, A.; Iglesias, B.; López, S. Tetrahedron Lett. 1992, 33, 6205-6208.
74. (b) Torrado, A.; López, S.; Alvarez, R.; de Lera, A. R. Synthesis 1995, 285-293.
75. (c) Nicolaou, K. C.; Ramphal, J. Y.; Palazon, J. M.; Spanevello, R. A. Angew. Chem. Int. Ed. Engl. 1989, 28, 587-588.
76. (a) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127-3128.
77. (b) Batt, D. G.; Houghton, G. C.; Daneker, W. F.; Jadhav, P. K. J. Org. Chem. 2000, 65, 8100-8104.
78. (a) Soundararajan, R.; Matteson, D. S. J. Org. Chem. 1990, 55, 2274-2275.
79. (b) Brown, H. C.; Basavaiah, D.; Bhat, N. G. Organometallics 1983, 2, 1309-1311.
80. (a) Miyaura, N.; Suginome, H.; Suzuki, A. Tetrahedron Lett. 1984, 25, 761-764.
81. (b) Miyaura, N.; Satoh, Y.; Hara, S.; Suzuki, A. Bull. Chem. Soc. Jpn. 1986, 59, 2029-2031.
82. Vaultier, M.; Truchet, F.; Carboni, B.; Hoffmann, R. W.; Denne, I. Tetrahedron Lett. 1987, 28, 4169-4172.
83. 2BH= Di(isopropylprenyl)borane; Kalinin, A. V.; Scherer, S.; Snieckus, V. Angew. Chem., Int. Ed. 2003, 42, 3399-3404.
84. (a) Boger, D. L.; Ichikawa, S. Zhong, W. J. Am. Chem. Soc. 2001, 123, 4161-4167.
85. (b) Uemura, I.; Miyagawa, H.; Ueno, T. Tetrahedron 2002, 58, 2351-2358.
86. (c) Uenishi, J.-i.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1996, 61, 5716-5717.
87. (d) Uenishi, J.-i.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1998, 63, 8965-8975.
88. Molander, G. A.; Felix, L., unpublished results.
89. For DDQ-deprotection of benzyl groups on olefinic substrates, see: (a) Crimmins, M. T.; DeBaillie, A. C. Org. Lett. 2003, 5, 3009-3011.
90. (b) Meng, D.; Tan, Q.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1999, 38, 3197-3201.