Synthesis of the bicyclic welwitindolinone core via an alkylation/ cyclization cascade reaction

Organic Letters

Volumn 11, Issue 22, 2009, Pages 5330-5333

  Brailsford, John A ^a   Lauchli, Ryan ^a   Shea, Kenneth J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; INDOLE DERIVATIVE; NITRILE; WELWITINDOLINONE A; WELWITINDOLINONE B; WELWITINDOLINONE C ISOTHIOCYANATE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; ALKYLATION; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; INDOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRILES; STEREOISOMERISM;

EID: 70749128677     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902173g     Document Type: Article

References (40)

1. Longley, D.; Johnston, P. J. Pathol. 2005, 205, 275-292.
2. Szakacs, G.; Paterson, J. K.; Ludwig, J. A.; Booth-Genthe, C.; Gottesman, M. M. Nat. Rev. Drug Discov. 2006, 5, 219-234.
3. Aller, S. G.; Yu, J.; Ward, A.; Weng, Y.; Chittaboina, S.; Zhuo, R.; Harrell, P. M.; Trinh, Y. T.; Zhang, Q.; Urbatsch, I. L.; Chang, G. Science 2009, 323, 1718-1722.
4. 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, 9935-9942.
5. Smith, C.; Zilfou, J.; Stratmann, K.; Patterson, G.; Moore, R. Mol. Pharmacol. 1995, 47, 241-247.
6. Zhang, X.; Smith, C Mol. Pharmacol. 1996, 49, 288-294.
7. (a) Reisman, S. E.; Ready, J. M.; Weiss, M. M.; Hasuoka, A.; Hirata, M.; Tamaki, K.; Ovaska, T. V.; Smith, C. J.; Wood, J. L. J. Am. Chem. Soc. 2008, 130, 2087-2100.
8. (b) Reisman, S. E.; Ready, J. M.; Hasuoka, A.; Smith, C. J.; Wood, J. L. J. Am. Chem. Soc. 2006, 128, 1448-1449.
9. (a) Baran, P. S.; Richter, J. M. J. Am. Chem Soc. 2005, 127, 15394-15396.
10. (b) Baran, P. S.; Maimone, T. J.; Richter, J. M. Nature 2007, 446, 404-408.
11. Reviews: (a) Avendaño, C; Menéndez, J. C. Curr. Org. Synth. 2004, 1, 65-82.
12. (b) Menendez, J. C. Top. Heterocycl. Chem. 2007, 11, 63-101.
13. (c) Brown, L. E.; Konopelski, J. P. Org. Prep. Proced. Int. 2008, 40, 411-445.
14. (a) MacKay, J. A.; Bishop, R. L.; Rawal, V. H. Org. Lett. 2005, 7, 3421-3424.3
15. (b) Greshock, T. J.; Funk, R. L. Org. Lett. 2006, 8, 2643-2645.
16. (c) Baudoux, J.; Blake, A. J.; Simpkins, N. S. Org. Lett. 2005, 7, 4087-4089.
17. (d) Boissel, V.; Simpkins, N. S.; Bhalay, G. Tetrahedron Lett. 2009, 50, 3283-3286.
18. (e) Boissel, V.; Simpkins, N. S.; Bhalay, G.; Blake, A. J.; Lewis, W. Chem. Commun. 2009, 1398-1400.
19. (f) Tian, X.; Huters, A. D.; Douglas, C. J.; Garg, N. K. Org. Lett. 2009, 11, 2349-2351.
20. (g) Trost, B. M.; McDougall, P. J. Org. Lett. 2009, 11, 3782-3785.
21. (h) Jung, M. E.; Slowinski, F. Tetrahedron Lett. 2001,42, 6835-6838.
22. (i) Konopelski, J. P.; Deng, H.; Schiemann, K.; Keane, J. M.; Olmstead, M. M. Synlett 1998, 1105-1107.
23. (j) Deng, H.; Konopelski, J. P. Org. Lett. 2001, 3, 3001-3004..
24. (k) 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, 6326-6327.
25. l) Lauchli, R.; Shea, K. J.. Org. Lett. 2006, 8, 5287-5289
26. Madera, A. M.; Weikert, R. J. PCT Int. Appl. WO 2004026831, 2004.
27. (a) Moyer, M. P.; Shiurba, J. F.; Rapoport, H. J. Org. Chem. 1986, 51, 5106-5110.
28. (b) Nicolaou, K. C.; Snyder, S. A.; Huang, X.; Simonsen, K. B.; Koumbis, A. E.; Bigot, A. J. Am. Chem. Soc. 2004, 126, 10162-10173.
29. Vazquez, E.; Payack, J. F. Tetrahedron Lett. 2004, 45, 6549-6550.
30. Previous reported syntheses of 19: (a) Kosuge, T.; Ishida, H.; Inaba, A.; Nukaya, H. Chem. Pharm. Bull. 1985, 33, 1414-1418.
31. (b) Chao, H. J. PCT Int. Appl. WO 2005113511, 2005.
32. (c) Xie, J.; Sun, J.; Zhang, G.; Houghten, R. A.; Yu, Y. J. Comb. Chem. 2007, 9, 566-568.
33. Cortese, N. A.; Ziegler, C B.; Hrnjez, B. J.; Heck, R. F. J. Org. Chem. 1978, 43, 2952-2958.
34. (a) Urban, F. J.; Jasys, V. J.; Raggon, J. W.; Buzon, R. A.; Hill, P. D.; Eggler, J. F.; Weaver, J. D. Synth. Commun. 2003, 33, 2029-2043.
35. For a discussion of these furan alcohols in solvolysis reactions. Noyce, D. S.; Pavez, H. J. J. Org. Chem. 1972, 37, 2620-2623.
36. Brion, F. Tetrahedron Lett. 1982, 23, 5299-5302.
37. Kanoh, N.; Ishihara, J.; Yamamoto, Y.; Murai, A. Synthesis 2000, 1878-1893.
38. Ellis, J. M.; Overman, L. E.; Tanner, H. R.; Wang, J. J. Org. Chem. 2008, 73, 9151-9154.
39. Related rearrangements have been reported :(a) Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136.
40. (b) Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246-3247.