Directed oxidative cyclizations to C2- or C4-positions of indole: Efficient construction of the bicyclo[4.3.1]decane core of welwitindolinones

Organic Letters

Volumn 13, Issue 12, 2011, Pages 3214-3217

  Bhat, Vikram ^a   MacKay, James A ^a   Rawal, Viresh H ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE; INDOLE ALKALOID; INDOLE DERIVATIVE; OXINDOLE; WELWITINDOLINONE B ISOTHIOCYANATE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CHLORINE; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; INDOLE ALKALOIDS; INDOLES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79958818180     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201122f     Document Type: Article

References (45)

1. Stratmann, K.; Moore, R. E.; Bonjouklian, R.; Deeter, J. B.; Patterson, G. M. L.; Shaffer, S.; Smith, C. D.; Smitka, T. A. J. Am. Chem. Soc. 1994, 116, 9935
2. Jimenez, J. I.; Huber, U.; Moore, R. E.; Patterson, G. M. L. J. Nat. Prod. 1999, 62, 569
3. For approaches toward welwitindolinone alkaloids, see: Konopelski, J. P.; Deng, H.; Schiemann, K.; Keane, J. M.; Olmstead, M. M. Synlett 1998, 1105
4. Wood, J. L.; Holubec, A. A.; Stoltz, B. M.; Weiss, M. M.; Dixon, J. A.; Doan, B. D.; Shamji, M. F.; Chen, J. M.; Heffron, T. P. J. Am. Chem. Soc. 1999, 121, 6326
5. Kaoudi, T.; Ouiclet-Sire, B.; Seguin, S.; Zard, S. Z. Angew. Chem., Int. Ed. 2000, 39, 731
6. Deng, H.; Konopelski, J. P. Org. Lett. 2001, 3, 3001
7. Jung, M. E.; Slowinski, F. Tetrahedron Lett. 2001, 42, 6835
8. López-Alvarado, P.; García-Granda, S.; Àlvarez- Rúa, C.; Avendaño, C. Eur. J. Org. Chem. 2002, 1702
9. Ready, J. M.; Reisman, S. E.; Hirata, M.; Weiss, M. M.; Tamaki, K.; Ovaska, T. V.; Wood, J. L. Angew. Chem., Int. Ed. 2004, 43, 1270
10. Baudoux, J.; Blake, A. J.; Simpkins, N. S. Org. Lett. 2005, 7, 4087
11. Greshock, T. J.; Funk, R. L. Org. Lett. 2006, 8, 2643
12. Lauchli, R.; Shea, K. J. Org. Lett. 2006, 8, 5287
13. Xia, J.; Brown, L. E.; Konopelski, J. P. J. Org. Chem. 2007, 72, 6885
14. Richter, J. M.; Ishihara, Y.; Masuda, T.; Whitefield, B. W.; Llamas, T.; Pohjakallio, A.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 17938
15. Boissel, V.; Simpkins, N. S.; Bhalay, G.; Blake, A. J.; Lewis, W. Chem. Commun. 2009, 1398
16. Boissel, V.; Simpkins, N. S.; Bhalay, G. Tetrahedron Lett. 2009, 50, 3283
17. Tian, X.; Huters, A. D.; Douglas, C. J.; Garg, N. K. Org. Lett. 2009, 11, 2349
18. Trost, B. M.; McDougall, P. J. Org. Lett. 2009, 11, 3782
19. Brailsford, J. A.; Lauchli, R.; Shea, K. J. Org. Lett. 2009, 11, 5330
20. Freeman, D. B. Tetrahedron 2010, 66, 6647
21. Heidebrecht, R. W., Jr.; Gulledge, B.; Martin, S. F. Org. Lett. 2010, 12, 2492
22. Ruiz, M.; López-Alvarado, P.; Menéndez, J. C. Org. Biomol. Chem. 2010, 8, 4521
23. MacKay, J. A.; Bishop, R. L.; Rawal, V. H. Org. Lett. 2005, 7, 3421
24. Bhat, V.; Allan, K. M.; Rawal, V. H. J. Am. Chem. Soc. 2011, 133, 5798
25. Artis, D. R.; Cho, I.-S.; Muchowski, J. M. Can. J. Chem. 1992, 70, 1838
26. Chuang, C. P.; Wang, S. F. Tetrahedron Lett. 1994, 35, 1283
27. Tsai, A.-I.; Lin, C.-H.; Chuang, C. P. Heterocycles 2005, 65, 2381
28. Magolan, J.; Kerr, M. A. Org. Lett. 2006, 8, 4561
29. Magolan, J.; Carson, C. A.; Kerr, M. A. Org. Lett. 2008, 10, 1437
30. Chen, P.; Cao, L.; Tian, W.; Wang, X.; Li, C. Chem. Commun. 2010, 46, 8436
31. For other methods, see: Tucker, J. W.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 368
32. Tanaka, M.; Ubukata, M.; Matsuo, T.; Yasue, K.; Matsumoto, K.; Kajimoto, Y.; Ogo, T.; Inaba, T. Org. Lett. 2007, 9, 3331
33. Muratake, H.; Natsume, M. Tetrahedron 1990, 46, 6331
34. Sakagami, M.; Muratake, H.; Natsume, M. Chem. Pharm. Bull. 1994, 42, 1393
35. Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1983, 24, 5425
36. For comprehensive reviews on oxidative cyclization reactions, see: Snider, B. B. Chem. Rev. 1996, 96, 339
37. Snider, B. B. Manganese(III)-Based Oxidative Free-Radical Cyclizations. In Transition Metals for Organic Synthesis, 2 nd ed.; Beller, M.; Bolm, C., Ed.; Wiley-VCH Verlag: Weinheim, 2004; Vol. 1, pp 483-490.
38. For synthesis of structurally similar bicyclo[3.3.1]nonanes, see: Trost, B. M.; Fortunak, J. M. D. Organometallics 1982, 1, 7
39. Butkus, E.; Berg, U.; Malinauskiene, J.; Sandstroem, J. J. Org. Chem. 2000, 65, 1353
40. Butkus, E.; Malinauskiene, J.; Stoncius, S. Org. Biomol. Chem. 2003, 1, 391
41. Baranova, T. Y.; Zefirova, O. N.; Averina, N. V.; Boyarskikh, V. V.; Borisova, G. S.; Zyk, N. V.; Zefirov, N. S. Russ. J. Org. Chem. 2007, 43, 1196
42. See the Supporting Information for details.
43. Collins, D. J.; Cullen, J. D.; Fallon, G. D.; Gatehouse, B. M. Aust. J. Chem. 1984, 37, 2279
44. Krawczuk, P. J.; Schöne, N.; Baran, P. S. Org. Lett. 2009, 11, 4774
45. Oxindole 25 was obtained as a single diastereomer; however, the absolute configuration at the C3-position was not determined.