2-Nitrophenyl isocyanide as a versatile convertible isocyanide: Rapid access to a fused γ-lactam β-lactone bicycle

Journal of Organic Chemistry

Volumn 73, Issue 11, 2008, Pages 4198-4204

  Gilley, Cynthia B ^a   Kobayashi, Yoshihisa ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLES; CHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

AMERICAN CHEMICAL SOCIETY (ACS); CATALYTIC AMOUNTS; CHEMICAL EQUATIONS; EFFICIENT SYNTHESIS; ISOCYANIDE; LACTONIZATION; PROTEASOME INHIBITORS; PYROGLUTAMIC ACIDS; UGI REACTION;

CYANIDES;

2 NITROPHENYL ISOCYANIDE; BENZOTRIAZOLE DERIVATIVE; CINNABARAMIDE DERIVATIVE; CYANIDE; GAMMA LACTAM DERIVATIVE; LACTACYSTIN BETA LACTONE; LACTONE DERIVATIVE; OXOACID; PROTEASOME INHIBITOR; PYROGLUTAMIC ACID DERIVATIVE; SALINOSPORAMIDE A;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; LACTONIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 44949169626     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800486k     Document Type: Article

References (86)

1. (a) Omura, S.; Fujimoto, T.; Otoguru, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113-116.
2. (b) Omura, S.; Matsuzaki, K.; Fujimoto, T.; Kosuge, K.; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117-118.
3. Isolation of salinosporamide A: (a) Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355-357.
4. For congeners of salinosporamide A, see: (b) Williams, P. G.; Buchanan, G. O.; Feling, R. H.; Kauffman, C. A.; Jensen, P. R. J. Org. Chem. 2005, 70, 6196-6203.
5. (c) Stadler, M.; Bitzer, J.; Mayer-Bartschmid, A.; Mueller, H.; Benet-Buchholz, J.; Gantner, F.; Tichy, H. V.; Reinemer, P.; Bacon, K. B. J. Nat. Prod. 2007, 70, 246-252.
6. (d) Reed, K. A.; Manam, R. R.; Mitchell, S. S.; Xu, J.; Teisan, S.; Chao, T. H.; Deyanat-Yazdi, G.; Neuteboom, S. T. C.; Lam, K. S.; Potts, B. C. M. J. Nat. Prod. 2007, 70, 269-276.
7. Cinnabaramides, A.-G.; Stadler, M.; Bitzer, J.; Mayer-Bartschmid, A.; Muller, H.; Benet-Buchholz, J.; Gantner, F.; Tichy, H. V.; Reinemer, P.; Bacon, K. B. J. Nat. Prod. 2007, 70, 246-52.
8. Kyle, R. A.; Rajkumar, S. V. N. Engl. J. Med. 2004, 351, 1860-1873.
9. (a) Chauhan, D.; Catley, L.; Li, G.; Podar, K.; Hideshima, T.; Velonkar, M.; Mitsiades, C.; Mitsiades, N.; Yasui, H.; Letai, A.; Ovaa, H.; Berkers, C.; Nicholson, B.; Chao, T. H.; Neuteboom, S. T.; Richardson, P.; Palladino, M. A.; Anderson, K. C. Cancer Cell 2005, 8, 407-419.
10. (b) Macherla, V. R.; Michell, S. S.; Manam, R. R.; Reed, K. A.; Chao, T. H.; Nicholson, B.; Deyanat-Yazdi, G.; Mai, B.; Jensen, P. R.; Fenical, W.; Neuteboom, S. T. C.; Lam, K. S.; Palladino, M. A.; Potts, B. C. M. J. Med. Chem. 2005, 48, 3684-3687.
11. Groll, M.; Ditzel, L.; Lowe, J.; Stock, D.; Bochtler, M.; Bartunik, H. D.; Huber, R. Nature 1997, 386, 463-471.
12. Groll, M.; Huber, R.; Potts, B. C. M. J. Am. Chem. Soc. 2006, 128, 5136-5141.
13. (a) Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677-10678.
14. (b) Sunazuka, T.; Nagamitsu, T.; Matsuzaki, K.; Tanaka, H.; Omura, S.; Smith, A. B., III J. Am. Chem. Soc. 1993, 115, 5302.
15. (c) Uno, H.; Baldwin, J. E.; Russell, A. J. Am. Chem. Soc. 1994, 116, 2139-2140.
16. (d) Chida, N.; Takeoka, J.; Tsutsumi, N.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1995, 793-794.
17. (e) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III J. Am. Chem. Soc. 1996, 118, 3584-3590.
18. (f) Chida, N.; Takeoka, J.; Ando, K.; Tsutsumi, N.; Ogawa, S. Tetrahedron 1997, 53, 16287-16298.
19. (g) Kang, S. H.; Jun, H.-S. Chem. Commun. 1998, 1929-1930.
20. (h) Corey, E. J.; Li, W.-D.; Nagamitsu, T. Angew. Chem., Int. Ed. 1998, 37, 1676-1679.
21. (i) Corey, E. J.; Li, W.; Reichard, G. A. J. Am. Chem. Soc. 1998, 120, 2330-2336.
22. (j) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 8043-8046.
23. (k) Panek, J. S.; Masse, C. E. Angew. Chem., Int. Ed. 1999, 38, 1093-1095.
24. (l) Soucy, F.; Grenier, L.; Behnke, M. L.; Destree, A. T.; McCormack, T. A.; Adams, J.; Plamondon, L. J. Am. Chem. Soc. 1999, 121, 9967-9976.
25. (m) Iwama, S.; Gao, W.-G.; Shinada, T.; Ohfune, Y. Synlett 2000, 1631-1633.
26. (n) Green, M.; Prodger, J. C.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6609-6611.
27. (o) Saravanan, P.; Corey, E. J. J. Org. Chem. 2003, 68, 2760-2764.
28. (p) Brennan, C. J.; Pattenden, G.; Rescourio, G. Tetrahedron Lett. 2003, 44, 8757-8760.
29. (q) Donohoe, T. J.; Sintim, H. O.; Sisangia, L.; Harling, J. D. Angew. Chem., Int. Ed. 2004, 43, 2293-2296.
30. (r) Ooi, H.; Ishibashi, N.; Iwabuchi, Y.; Ishihara, J.; Hatakeyama, S. J. Org. Chem. 2004, 69, 7765-7768.
31. (s) Donohoe, T. J.; Sintim, H. O.; Sisangia, L.; Ace, K. W.; Guyo, P. M.; Cowley, A.; Harling, J. D. Chem. - Eur. J. 2005, 11, 4227-4238.
32. (t) Wardrop, D. J.; Bowen, E. G. Chem. Commun. 2005, 5106-5108.
33. (u) Reddy, L. R.; Fournier, J.-F.; Reddy, B. V. S.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 8974-8976.
34. (v) Reddy, L. R.; Saravanan, P.; Fournier, J.-F.; Reddy, B. V. S.; Corey, E. J. Org. Lett. 2005, 7, 2703-2705.
35. (w) Hayes, C. J.; Sherlock, A. E.; Selby, M. D. Org. Biomol. Chem. 2006, 4, 193-195.
36. (x) Fukuda, N.; Sasaki, K.; Sastry, T. V. R. S.; Kanai, M.; Shibasaki, M. J. Org. Chem. 2006, 71, 1220-1225.
37. (y) Balskus, E. P.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 6810-6812.
38. (z) Yoon, C. H.; Flanigan, K. L.; Yoo, K. S.; Jung, K. W. Eur. J. Org. Chem. 2007, 1, 37-39.
39. (aa) Legeay, J. C.; Langlois, N. J. Org. Chem. 2007, 72, 10108-10113.
40. (bb) Hayes, C. J.; Sherlock, A. E.; Green, M. P.; Wilson, C.; Blake, A. J.; Matthew, D.; Selby, M. D.; Prodger, J. C. J. Org. Chem. 2008, 73, 2041-2051.
41. For a recent review, see: (cc) Shibasaki, M.; Kanai, M.; Fukuda, N. Chem. Asian J. 2007, 2, 20-38.
42. For salinosporamide A total syntheses, see: (a) Reddy, L. R.; Saravanan, P.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 6230-6231.
43. (b) Reddy, L. R.; Fournier, J. F.; Reddy, B. V. S.; Corey, E. J. Org. Lett. 2005, 7, 2699-2701.
44. (c) Reddy, L. R.; Fournier, J. F.; Reddy, B. V. S.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 8974-8976.
45. (d) Endo, A.; Danishefsky, S. J. J. Am. Chem. Soc. 2005, 127, 8298-8299.
46. (e) Mullholand, N. P.; Pattenden, G.; Walters, I. A. S. Org. Biomol. Chem. 2006, 4, 2845-2846.
47. (f) Ling, T.; Macherla, V. R.; Manam, R. R.; McArthur, K. A.; Potts, B. C. M. Org. Lett. 2007, 9, 2289-2292.
48. Ma, G.; Nguyen, H.; Romo, D. Org. Lett. 2007, 9, 2143-2146.
49. (a) Isaacson, J.; Gilley, C. B.; Kobayashi, Y. J. Org. Chem. 2007, 72, 3913-3916.
50. (b) Tye, H.; Wittaker, M. Org. Biomol. Chem. 2004, 2, 813-815.
51. (c) Hulme, C.; Ma, L.; Cherrier, M. P.; Romano, J. J.; Morton, G.; Duquenne, C.; Salvino, J.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1883-1887.
52. (d) Hanusch-Kompa, C.; Ugi, I. Tetrahedron Lett. 1998, 39, 2725-2728.
53. (e) Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1997, 38, 359-362.
54. (f) Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591-5594.
55. (a) Gilley, C. B.; Buller, M. J.; Kobayashi, Y. Org. Lett. 2007, 9, 3631-3634.
56. (b) Vamos, M.; Ozboya, K.; Kobayashi, Y. Synlett 2007, 1595-1599.
57. (c) Kreye, O.; Westermann, B.; Wessjohann, L. A. Synlett 2007, 3188-3192.
58. The acidic conditions required to activate the (2,2-dimethoxyethyl) anilide to the N-acylindole intermediate with the convertible isocyanide, 1-isocyano-2-(2,2-dimethoxyethyl)benzene, in our previous synthesis caused unwanted N,O-acetal formation as the major product by reaction with the unprotected alcohols (see ref 12a).
59. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
60. For recent reviews on the application of N-acylbenzotriazoles in organic synthesis, see: (a) Katritzky, A. R.; Suzuki, K.; Wang, Z. Synlett 2005, 11, 1656-1665.
61. (b) Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev. 1998, 98, 409-548.
62. (a) Katritzky, A. R.; Ji, F. B.; Fan, W. Q.; Beretta, P.; Bertoldi, M. J. Heterocycl. Chem. 1992, 29, 1519-1523.
63. (b) Plummer, B. F.; Russell, S. R.; Reese, W. G.; Watson, W. H.; Krawiec, M. J. Org. Chem. 1991, 56, 3219-23.
64. (c) Hart, H.; Ok, D. J. Org. Chem. 1986, 51, 979-986.
65. We expected a single diastereomer in the Ugi reaction of ketacid 11 based on our previous studies (see ref 12a).
66. Hahn, F. E.; Plumed, C. G.; Muender, M.; Luegger, T. Chem. Eur. J. 2004, 10, 6285-6293.
67. (a) Maison, W.; Schlemminger, I.; Westerhoff, O.; Martens, J. Bioorg. Med. Chem. Lett. 2000, 8, 1343-1360.
68. (b) Maison, W.; Schlemminger, I.; Westerhoff, O.; Martens, J. Bioorg. Med. Chem. Lett. 1999, 9, 581-584.
69. Newman, M. S. J. Am. Chem. Soc. 1950, 72, 4783-4786.
70. The CIF file of the X-ray analysis of compound 17 is available in the Supporting Information.
71. For use of the smiles rearrangement in Ugi reactions, see: (a) El Kaïm, L.; Grimaud, L.; Oble, J. Angew. Chem., Int. Ed. 2005, 44, 7691.
72. (b) El Kaïm, L.; Gizolme, M.; Grimaud, L. Org. Lett. 2006, 8, 2051-2053.
73. (c) El Kaïm, L.; Gizolme, M.; Grimaud, L.; Oble, J. J. Org. Chem. 2007, 72, 4169-4180.
74. 2 HCl, EtOH, heat. These conditions are compatible with the presence of unsaturated bonds as well as other functionality not compatible with hydrogenolysis.
75. Tanaka, K.; Shimazak, M.; Murakami, Y. Chem. Pharm. Bull. 1982, 30, 2714-2722.
76. Katritzky, A. R.; Le, K. N. B.; Khelashvili, L.; Mohapatra, P. P. J. Org. Chem. 2006, 71, 9861-9864.
77. Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574-2583.
78. (a) Katritzky, A. R.; Angrish, P. Synthesis 2006, 24, 4135-4142.
79. (b) Katritzky, A. R.; Meher, G.; Angrish, P. Chem. Biol. Drug Des. 2006, 68, 326-333.
80. (c) Katritzky, A. R.; Todadze, E.; Shestopalov, A. A.; Cusido, J.; Angrish, P. Chem. Biol. Drug Des. 2006, 68, 42-47.
81. (d) atritzky, A. R.; Todadze, E.; Cusido, J.; Angrish, P.; Shestopalov, A. A. Chem. Biol. Drug Des. 2006, 68, 37-41.
82. (e) Katritzky, A. R.; Angrish, P.; Suzuki, K. Synthesis 2006, 3, 411-424.
83. (f) Katritzky, A. R.; Jiang, R.; Suzuki, K. J. Org. Chem. 2005, 70, 4993-5000.
84. (g) Katritzky, A. R.; Angrish, P.; Huer, D.; Suzuki, K. Synthesis 2005, 3, 397-402.
85. (h) Katritzky, A. R.; Suzuki, K.; Singh, S. K. Synthesis 2004, 16, 2645-2652.
86. (i) Katritzky, A. R.; Shestopalov, A. A.; Suzuki, K. Synthesis 2004, 11, 1806-1813.