Total synthesis of (+)-isatisine A: Application of a silicon-directed mukaiyama-type [3 + 2]-annulation

Journal of Organic Chemistry

Volumn 80, Issue 6, 2015, Pages 2959-2971

  Lee, Jihoon ^a   Panek, James S ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; DIASTEREOSELECTIVE; FUNCTIONALIZED; NATURAL PRODUCTS; TETRA-HYDROFURAN; TETRAHYDROFURANS; TOTAL SYNTHESIS; UNSATURATED ALDEHYDES;

ORGANIC COMPOUNDS;

ALDEHYDE; ALKALOID; COPPER DERIVATIVE; CYCLOPROPANE DERIVATIVE; INDOLE DERIVATIVE; ISATISINE A; SILICON DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG; INDOLE ALKALOID; ISATIN; SILANE DERIVATIVE;

AMIDATION; ANNULATION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CONTROLLED STUDY; CYCLOADDITION; MUKAIYAMA REACTION; REACTION OPTIMIZATION; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

INDOLE ALKALOIDS; ISATIN; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM;

EID: 84925353206     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00051     Document Type: Article

References (65)

1. Liu, J.-F.; Jiang, Z.-Y.; Wang, R.-R.; Zheng, Y.-T.; Chen, J.-J.; Zhang, X.-M.; Ma, Y.-B. Org. Lett. 2007, 9, 4127-4129
2. Karadeolian, A.; Kerr, M. A. J. Org. Chem. 2010, 75, 6830-6841
3. Karadeolian, A.; Kerr, M. A. Angew. Chem., Int. Ed. 2010, 49, 1133-1135
4. Lee, J.; Panek, J. S. Org. Lett. 2011, 13, 502-505
5. Zhang, X.; Mu, T.; Zhan, F.; Ma, L.; Liang, G. Angew. Chem., Int. Ed. 2011, 50, 6164-6166
6. Wu, W.; Xiao, M.; Wang, J.; Li, Yi.; Xie, Z. Org. Lett. 2012, 14, 1624-1627
7. Kumar, C. V. S.; Puranik, V. G.; Ramana, C. V. Chem.-Eur. J. 2012, 18, 9601-9611
8. Patel, P.; Ramana, C. V. J. Org. Chem. 2012, 77, 10509-10515
9. For isolation of goinolactone F, see: Wang, S.; Zhang, Y.-J.; Chen, R.-Y.; Yu, D.-Q. J. Nat. Prod. 2002, 65, 835-841
10. For isolation of harringtonolide, see: Buta, J. G.; Flippen, J. L.; Lusby, W. R. J. Org. Chem. 1978, 49, 1002-1003
11. Kang, S. H.; Lee, S. B.; Park, C. M. J. Am. Chem. Soc. 2003, 125, 15748-15749
12. McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981-3019
13. Nakhla, J. S.; Kampf, J. W.; Wolfe, J. P. J. Am. Chem. Soc. 2006, 128, 2893-2901
14. Wolfe, J. P.; Rossi, M. A. J. Am. Chem. Soc. 2004, 126, 1620-1621
15. Asano, K.; Matsubara, S. J. Am. Chem. Soc. 2011, 133, 16711-16713
16. Chavre, S. N.; Choo, H.; Lee, J. K.; Pae, A. N.; Kim, Y.; Cho, Y. S. J. Org. Chem. 2008, 73, 7467-7471
17. Overman, L. E.; Pennington, L. D. J. Org. Chem. 2003, 68, 7143-7157
18. Loh, T.-P.; Hu, Q.-Y.; Tan, K.-T.; Cheng, H.-S. Org. Lett. 2001, 3, 2669-2672
19. Hanaki, N.; Link, J. T.; MacMillan, D. W.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223-226
20. Kollmann, S.; Frohlich, R.; Hoppe, D. Synthesis 2007, 883-892
21. Bruns, A.; Wibbeling, B.; Frohlich, R.; Hoppe, D. Synthesis 2006, 3111-3121
22. Paulsen, H.; Graeve, C.; Hoppe, D. Synthesis 1996, 145-148
23. Hoppe, D.; Kramer, T.; Erdbrugger, C. F.; Egert, E. Tetrahedron Lett. 1989, 30, 1233-1236
24. Mertz, E.; Tinsley, J. M.; Roush, W. R. J. Org. Chem. 2005, 70, 8035-8046
25. Tinsley, J. M.; Roush, W. R. J. Am. Chem. Soc. 2005, 127, 10818-10819
26. Peng, Z. H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945-2948
27. Angle, S. R.; El-Said, N. A. J. Am. Chem. Soc. 2002, 124, 3608-3613
28. Micalizio, G. C.; Roush, W. R. Org. Lett. 2001, 3, 1949-1952
29. Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461-464
30. Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868-9870
31. Smith, A. G.; Slade, M. C.; Johnson, J. S. Org. Lett. 2011, 13, 1996-1999
32. Pohlhaus, P. D.; Sanders, S. D.; Parsons, A. T.; Li, W.; Johnson, J. S. J. Am. Chem. Soc. 2008, 130, 8642-8650
33. Lowe, J. T.; Panek, J. S. Org. Lett. 2005, 7, 3231-3234
34. Huang, H.; Panek, J. S. J. Am. Chem. Soc. 2000, 122, 9836-9837
35. Lowe, J. T.; Youngsaye, W.; Panek, J. S. J. Org. Chem. 2006, 71, 3639-3642
36. Su, Q.; Panek, J. S. J. Am, Chem. Soc. 2004, 126, 2425-2430
37. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391-394
38. Zhao, H.; Pagenkopf, B. L. Chem. Commun. 2003, 2592-2593
39. Kim, J. H.; Lee, S.; Kwon, M.-G.; Park, Y. S.; Choi, S.-K.; Kwon, B.-M. Synth. Commun. 2004, 34, 1223-1228
40. Smith, M. B.; March, J. March's Advanced Organic Chemistry Reactions, Mechanisms, and Structure, 6 th ed.; Wiley-Interscience: New York, 2007; pp 218-219.
41. de Meijere, A. Angew. Chem., Int. Ed. 1979, 18, 809-826
42. Qin, H.-L.; Panek, J. S. Org. Lett. 2008, 10, 2477-2479
43. Wrona, I. E.; Gabarda, A. E.; Evano, G.; Panek, J. S. J. Am. Chem. Soc. 2005, 127, 15026-15027
44. Tron, G. C.; Pagliai, F.; Grosso, E. D.; Genazzani, A. A.; Sorba, G. J. Med. Chem. 2005, 48, 3260-3268
45. Slee, D. H.; Romano, S. J.; Yu, J.; Nguyen, T. N.; John, J. K.; Raheja, N. K.; Axe, F. U.; Jones, T. K.; Ripka, W. C. J. Med. Chem. 2001, 44, 2094-2107
46. Higuchi, K.; Sato, Y.; Tsuchimochi, M.; Sugiura, K.; Hatori, M.; Kawasaki, T. Org. Lett. 2009, 11, 197-199
47. Abid, M.; Teixeira, L.; Torok, B. Org. Lett. 2008, 10, 933-935
48. Skarpos, H.; Vorob'eva, D. V.; Osipov, S. N.; Odinets, I. L.; Breuer, E.; Roschenthaler, G.-V. Org. Biomol. Chem. 2006, 4, 3669-3674
49. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428
50. Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729
51. Denmark, S. E.; Hurd, A. R. J. Org. Chem. 2000, 65, 2875-2886
52. Comins, D.; Libby, A. H.; Al-awar, R. S.; Foti, C. J. J. Org. Chem. 1999, 64, 2184-2185
53. Roberson, C. W.; Woerpel, K. A. J. Org. Chem. 1999, 64, 1434-1435
54. Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317-337
55. Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487-6498
56. Adams, D. J.; Blake, A. J.; Cooke, P. A.; Gill, C. D.; Simpkins, N. S. Tetrahedron Lett. 2002, 58, 4603-4615
57. Marin, J.; Didierjean, C.; Aubry, A.; Briand, J.-P.; Guichard, G. J. Org. Chem. 2002, 67, 8440-8449
58. Semple, J. E.; Rydzewski, R. M.; Gardner, G. J. Org. Chem. 1996, 61, 7967-7972
59. Saleur, D.; Bouillon, J.-P.; Portella, C. J. Org. Chem. 2001, 66, 4543-4548
60. Haley, M. M.; Biggs, B.; Looney, W. A.; Gilbertson, R. D. Tetrahedron Lett. 1995, 36, 3457-3460
61. Billups, W. E.; Lee, G.-A.; Arney, B. E., Jr.; Whitmire, K. H. J.. Am. Chem. Soc. 1991, 113, 7980-7984
62. Fouque, E.; Rousseau, G.; Seyden-Penne, J. J. Org. Chem. 1990, 55, 4807-4817
63. Ager, D. J.; Fleming, I.; Patel, S. K. J. Chem. Soc., Perkin Trans. 1 1981, 2520-2526
64. Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616-5617
65. Niwa, H.; Hida, T.; Yamada, K. Tetrahedron Lett. 1981, 22, 4239-4240