Atom transfer radical cyclization of trichloroacetamides to electron-rich acceptors using Grubbs' catalysts: Synthesis of the tricyclic framework of FR901483

Journal of Organic Chemistry

Volumn 79, Issue 19, 2014, Pages 9365-9372

  Diaba, Faïza ^a   Martínez Laporta, Agustín ^a   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ATOM TRANSFER; ELECTRON-RICH; GRUBBS' CATALYST; RADICAL CYCLIZATIONS; TRICYCLIC FRAMEWORKS;

2 AZASPIRO[4.5]DECANE; ACETAMIDE DERIVATIVE; ACETIC ACID DERIVATIVE; ANISOLE DERIVATIVE; CARBENE; CARBON; DECANE; FR 901483; IMMUNOSUPPRESSIVE AGENT; RUTHENIUM CARBENE; TRICHLOROACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ATOM TRANSFER RADICAL CYCLIZATION; CATALYSIS; CHEMICAL BOND; CYCLIZATION; DRUG SYNTHESIS; KHARASCH ADDITION; RADICAL REACTION;

EID: 84907743128     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501110c     Document Type: Article

References (69)

1. Tallarico, J. A.; Malnick, L. M.; Snapper, M. L. J. Org. Chem. 1999, 64, 344-345
2. Simal, F.; Demonceau, A.; Noels, A. F. Tetrahedron Lett. 1999, 40, 5689-5693
3. Quayle, P.; Fengas, D.; Richards, S. Synlett 2003, 1797-1800
4. Faulkner, J.; Edin, C. D.; Fengas, D.; Preece, I.; Quayle, P.; Richards, S. N. Tetrahedron Lett. 2005, 46, 2381-2385
5. Seigal, B. A.; Fajardo, C.; Snapper, M. L. J. Am. Chem. Soc. 2005, 127, 16329-16332
6. Edlin, C. D.; Faulkner, J.; Quayle, P. Tetrahedron Lett. 2006, 47, 1145-1151
7. Edlin, C. D.; Faulkner, J.; Fengas, D.; Helliwell, M.; Knight, C. K.; House, D.; Parker, J.; Preece, I.; Quayle, P.; Taftery, J.; Richards, S. N. J. Organomet. Chem. 2006, 691, 5375-5382
8. McGonagle, F. I.; Brown, L.; Cooke, A.; Sutherland, A. Org. Biomol. Chem. 2010, 8, 3418-3425
9. For ring-closing olefin metathesis and radical cyclization as competing pathways, see: Schmidt, B.; Pohler, M.; Costisella, B. J. Org. Chem. 2004, 69, 1421-1424
10. Schmidt, B.; Pohler, M. J. Organomet. Chem. 2005, 690, 5552-5555
11. See also: Borguet, Y.; Sauvage, X.; Zaragoza, G.; Demonceau, A.; Delaude, L. Beilstein J. Org. Chem. 2010, 6, 1167-1173
12. Eckenhoff, W. T.; Pintauer, T. Catal. Rev. Sci. Eng. 2010, 52, 1-59
13. Muñoz-Molina, J. M.; Belderrain, T. R.; Pérez, P. J. Eur. J. Inorg. Chem. 2011, 3155-3164
14. Bonjoch, J.; Bradshaw, B.; Diaba, F. In Stereoselective Synthesis of Drugs and Natural Products; Andrushko, V.; Andrushhko, N., Eds.; Wiley-VCH: New York, 2013; pp 733-768.
15. Sandmeier, P.; Tamm, C. Helv. Chim. Acta 1990, 73, 975-984
16. Siddiqui, B. S.; Usmani, S. B.; Begum, S.; Siddiqui, S. Phytochemistry 1993, 33, 925-928
17. Hallock, Y. F.; Lu, H. S. M.; Clardy, J.; Strobel, G. A.; Sugawara, F.; Samsoedin, R.; Yoshida, S. J. Nat. Prod. 1993, 56, 747-754
18. Yang, Y.-L.; Chang, F.-R.; Wu, Y.-C. Helv. Chim. Acta 2004, 87, 1392-1399
19. Shigehisa, H.; Takayama, J.; Honda, T. Tetrahedron Lett. 2006, 47, 7301-7306
20. For a review on the synthesis of 2-azabicyclo[3.3.1]nonanes, see: Bonjoch, J.; Diaba, F.; Bradshaw, B. Synthesis 2011, 993-1018
21. Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara, M. J. Antibiot. 1996, 49, 37-44
22. For a review on the biology and synthesis of FR901483, see: Bonjoch, J.; Diaba, F. In Studies in Natural Products Chemistry, Bioactive Natural Products (Part L); Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 2005; Vol. 32, pp 3-60.
23. Rishton, G. M.; Schwarts, M. A. Tetrahedron Lett. 1988, 29, 2643-2646
24. Santra, S.; Andreana, P. R. Org. Lett. 2007, 9, 5035-5038
25. Pigge, F. C.; Dhanya, R.; Hoefgen, E. R. Angew. Chem., Int. Ed. 2007, 46, 2887-2890
26. Ovens, C.; Martin, N. G.; Procter, D. J. Org. Lett. 2008, 10, 1441-1444
27. Liang, J.; Chen, J.; Du, F.; Zeng, X.; Li, L.; Zhang, H. Org. Lett. 2009, 11, 2820-2823
28. Rozhkova, Y. S.; Khmelevskaya, K. A.; Shklyaev, Y. V.; Ezhikova, M. A.; Kodess, M. I. Russ. J. Org. Chem. 2012, 48, 69-77
29. Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 5985-5988
30. Ibarra-Rivera, T. R.; Gámez-Montaño, R.; Miranda, L. D. Chem. Commun. 2007, 3485-3487
31. Gámez-Montaño, R.; Ibarra- Rivera, T.; El Kaïm, L.; Miranda, L. D. Synthesis 2010, 1285-1290
32. Diaba, F.; Montiel, J. A.; Martinez-Laporta, A.; Bonjoch, J. Tetrahedron Lett. 2013, 54, 2619-2622
33. For studies of cyclization using Cu(I) catalysts, see: Diaba, F.; Martínez-Laporta, A.; Bonjoch, J.; Pereira, A.; Muñoz-Molina, J. M.; Pérez, J. P.; Belderrain, T. R. Chem. Commun. 2012, 48, 8799-8801
34. Quirante, J.; Escolano, C.; Diaba, F.; Bonjoch, J. J. Chem. Soc., Perkin Trans. 1 1999, 1157-1162
35. 2 as a catalyst to promote the cyclization of a trichloroacetamide upon a simple alkene: Li, Q.; Li, G.; Ma, S.; Feng, P.; Shi, Y. Org. Lett. 2013, 15, 2601-2603
36. Alcaide, B.; Almendros, P.; Luna, A. Chem. Rev. 2009, 109, 3817-3858
37. Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778-7786
38. Scheffer, G.; Seike, H.; Sorensen, E. J. Angew. Chem., Int. Ed. 2000, 39, 4593-4596
39. Ousmer, M.; Braun, N. A.; Bavoux, C.; Perrin, M.; Ciufolini, M. A. J. Am. Chem. Soc. 2001, 123, 7534-7538
40. Maeng, J.-H.; Funk, R. L. Org. Lett. 2001, 3, 1125-1128
41. Kan, T.; Fujimoto, T.; Ieda, S.; Asoh, Y.; Kitaoka, H.; Fukuyama, T. Org. Lett. 2004, 6, 2729-2731
42. Brummond, K. M.; Hong, S.-P. J. Org. Chem. 2005, 70, 907-916
43. Carson, C. A.; Kerr, M. A. Org. Lett. 2009, 11, 777-779
44. Ieda, S.; Masuda, A.; Kariyama, M.; Wakimoto, T.; Asakawa, T.; Fukuyama, T.; Kan, T. Heterocycles 2012, 86, 1071-1092
45. Ma, A.-J.; Tu, Y.-Q.; Peng, J.-B.; Dou, Q.-Y.; Hou, S.- H.; Zhang, F.-M.; Wang, S.-H. Org. Lett. 2012, 14, 3604-3607
46. Huo, H.-H.; Xia, X.-E.; Zhang, H.-K.; Huang, P.-Q. J. Org. Chem. 2013, 78, 455-465
47. Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280-8281
48. Wardrop, D. J.; Zhang, W. Org. Lett. 2001, 3, 2353-2356
49. Suzuki, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 3013-3015
50. Bonjoch, J.; Diaba, F.; Puigbó, G.; Peidró, E.; Solé, D. Tetrahedron Lett. 2003, 44, 8387-8390
51. Solé, D.; Urbaneja, X.; Bonjoch, J. Adv. Synth. Catal. 2004, 346, 1646-1650
52. Kropf, J. E.; Meigh, I. C.; Bebbington, W. P.; Weinreb, S. M. J. Org. Chem. 2006, 71, 2046-2055
53. Kaden, S.; Reissig, H.-U. Org. Lett. 2006, 8, 4763-4766
54. Simila, S. T. M.; Martin, S. F. J. Org. Chem. 2007, 72, 5342-5349
55. Diaba, F.; Ricou, E.; Solé, D.; Teixido, E.; Valls, N.; Bonjoch, J. ARKIVOC 2007, 320-330
56. Asari, A.; Angelov, P.; Auty, J. M.; Hayes, C. Tetrahedron Lett. 2007, 48, 2631-2634
57. Seike, H.; Sorensen, E. J. Synlett 2008, 695-701
58. Puppala, M.; Murali, A.; Baskaran, S. Chem. Commun. 2012, 48, 5778-5780
59. Perreault, S.; Rovis, T. Synthesis 2013, 45, 719-728
60. Zhang, J.; Wang, Y.-Q.; Wang, X.-W.; Li, W.-D. Z. J. Org. Chem. 2013, 78, 6154-6162
61. Yazici, A.; Pyne, S. G. Org. Lett. 2013, 15, 5878-5881
62. Ricou, E. Ph.D. Thesis, University of Barcelona, 2007.
63. Bonjoch, J.; Diaba, F.; Puigbó, G.; Solé, D.; Segarra, V.; Santamaria, L.; Beleta, J.; Ryder, H.; Palacios, J.-M. Bioorg. Med. Chem. 1999, 7, 2891-2897
64. Diaba, F.; Puigbó, G.; Bonjoch, J. Eur. J. Org. Chem. 2007, 3038-3044
65. Diaba, F.; Ricou, E.; Bonjoch, J. Tetrahedron Asymmetry 2006, 17, 1437-1443
66. Katakawa, K.; Kitajima, M.; Yamaguchi, K.; Takayama, H. Heterocycles 2006, 69, 223-229
67. Kolocouris, A. Tetrahedron Lett. 2007, 48, 2117-2122
68. Atanasova, I.; Petrov, I.; Mollov, N. Synth. Commun. 1989, 19, 147-153
69. Diaba, F.; Martínez-Laporta, A.; Bonjoch, J. Eur. J. Org. Chem. 2014, 2371-2378