Iridium-Catalyzed Enantioselective Indole Cyclization: Application to the Total Synthesis and Absolute Stereochemical Assignment of (-)-Aspidophylline A

Angewandte Chemie - International Edition

Volumn 55, Issue 12, 2016, Pages 4044-4048

  Jiang, Shi Zhi ^a   Zeng, Xue Yi ^a,b   Liang, Xiao ^a,b   Lei, Ting ^a   Wei, Kun ^a   Yang, Yu Rong ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

cyclizations; enantioselectivity; indoles; iridium; total synthesis

Indexed keywords

ACTIVATION ANALYSIS; CHEMICAL ACTIVATION; ENANTIOSELECTIVITY; IRIDIUM; POLYCYCLIC AROMATIC HYDROCARBONS; SYNTHESIS (CHEMICAL);

ABSOLUTE CONFIGURATION; ALLYLIC ALKYLATION; CYCLIZATIONS; ENANTIOSELECTIVE TOTAL SYNTHESIS; HETERONUCLEOPHILES; INDOLES; LEWIS-ACID ACTIVATION; TOTAL SYNTHESIS;

CYCLIZATION;

EID: 84960333438     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201511549     Document Type: Article

References (93)

1. A. Ramirez, S. Garcia-Rubio, Curr. Med. Chem. 2003, 10, 1891;
2. T. S. Kam, Alkaloids Chem. Biol. Perspect. 1999, 14, 285;
3. H. Arai, Y. Hirasawa, A. Rahman, I. Kusumawati, N. C. Zaini, S. Sato, C. Aoyama, J. Takeo, H. Morita, Bioorg. Med. Chem. 2010, 18, 2152;
4. H. L. Pearce, in The Alkaloids, Vol. 37 (Eds.:, A. Brossi, M. Suffness,), Academic Press, San Diego, 1990, p. 145;
5. R. Eckermann, T. Gaich, Synthesis 2013, 45, 2813;
6. J. M. Smith, J. Moreno, B. W. Boal, N. K. Garg, Angew. Chem. Int. Ed. 2015, 54, 400;
7. Angew. Chem. 2015, 127, 410.
8. G. Subramaniam, O. Hiraku, M. Hayashi, T. Koyano, K. Komiyama, T.-S. Kam, J. Nat. Prod. 2007, 70, 1783.
9. L. Zu, B. W. Boal, N. K. Garg, J. Am. Chem. Soc. 2011, 133, 8877.
10. J. M. Smith, J. Moreno, B. W. Boal, N. K. Garg, J. Org. Chem. 2015, 80, 8954.
11. M. Teng, W. Zi, D. Ma, Angew. Chem. Int. Ed. 2014, 53, 1814;
12. Angew. Chem. 2014, 126, 1845.
13. W. Ren, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2014, 53, 1818;
14. Angew. Chem. 2014, 126, 1849.
15. P. S. Baran, J. M. Richter, J. Am. Chem. Soc. 2004, 126, 7450;
16. P. S. Baran, J. M. Richter, J. Am. Chem. Soc. 2005, 127, 15394;
17. Z. Zuo, W. Xie, D. Ma, J. Am. Chem. Soc. 2010, 132, 13226;
18. W. Zi, Z. Zuo, D. Ma, Acc. Chem. Res. 2015, 48, 702.
19. K. Fujimoto, Y. Tokuda, Y. Matsubara, H. Maekawa, T. Mizuno, I. Nishiguchi, Tetrahedron Lett. 1995, 36, 7483;
20. S. P. Chavan, Y. T. Subbarao, Tetrahedron Lett. 1999, 40, 5073;
21. M. R. P. Norton Matos, C. A. M. Afonso, R. A. Batey, Tetrahedron Lett. 2001, 42, 7007;
22. L. Le Corre, J. C. Kizirian, C. Levraud, J. L. Boucher, V. Bonnet, H. Dhimane, Org. Biomol. Chem. 2008, 6, 3388;
23. F. Drouet, J. Zhu, G. Masson, Adv. Synth. Catal. 2013, 355, 3563.
24. Q. Li, G. Li, S. Ma, P. Feng, Y. Shi, Org. Lett. 2013, 15, 2601.
25. M. Zhang, X. Huang, L. Shen, Y. Qin, J. Am. Chem. Soc. 2009, 131, 6013;
26. W. Zi, W. Xie, D. Ma, J. Am. Chem. Soc. 2012, 134, 9126;
27. B. D. Horning, D. W. C. MacMillan, J. Am. Chem. Soc. 2013, 135, 6442.
28. X.-H. Cai, Q.-G. Tan, Y.-P. Liu, T. Feng, Z.-Z. Du, W.-Q. Li, X.-D. Luo, Org. Lett. 2008, 10, 577;
29. G. L. Adams, P. J. Carroll, A. B. Smith, J. Am. Chem. Soc. 2012, 134, 4037;
30. M. W. Smith, S. A. Snyder, J. Am. Chem. Soc. 2013, 135, 12964.
31. J. M. Smith, J. Moreno, B. W. Boal, N. K. Garg, J. Am. Chem. Soc. 2014, 136, 4504.
32. Almost at the same time of our submission, the group of Garg submitted their new work on the syntheses of akuammiline alkaloids. See:, J. Moreno, E. Picazo, L. A. Morrill, J. M. Smith, N. K. Garg, J. Am. Chem. Soc. 2016, 138, 1162.
33. S. B. Jones, B. Simmons, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 13606;
34. S. B. Jones, B. Simmons, A. Mastracchio, D. W. C. MacMillan, Nature 2011, 475, 183.
35. The group of Overman has reported a palladium-catalyzed tandem enantioselective intramolecular Heck/iminium cyclization which was utilized to accomplish the total synthesis of Strychnos alkaloid (+)-minfienisne, see:, A. B. Dounay, L. E. Overman, A. D. Wrobleski, J. Am. Chem. Soc. 2005, 127, 10186.
36. B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395;
37. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
38. Z. Lu, S. Ma, Angew. Chem. Int. Ed. 2008, 47, 258;
39. Angew. Chem. 2008, 120, 264;
40. J. D. Weaver, A. Recio, A. J. Grenning, J. A. Tunge, Chem. Rev. 2011, 111, 1846;
41. C.-X. Zhuo, C. Zheng, S.-L. You, Acc. Chem. Res. 2014, 47, 2558;
42. G. Helmchen, U. Kazmaier, S. Förster, in Catalytic Asymmetric Synthesis (Ed., I. Ojima,), Wiley, New York, 2010, p. 497.
43. A. V. Malkov, S. L. Davis, I. R. Baxendale, W. L. Mitchell, P. Kočovský, J. Org. Chem. 1999, 64, 2751.
44. M. Bandini, A. Melloni, A. Umani-Ronchi, Org. Lett. 2004, 6, 3199;
45. M. Bandini, A. Melloni, F. Piccinell, R. Sinisi, S. Tommasi, A. Umani-Ronchi, J. Am. Chem. Soc. 2006, 128, 1424;
46. M. Kimura, M. Futamata, R. Mukai, Y. Tamaru, J. Am. Chem. Soc. 2005, 127, 4592;
47. B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314;
48. N. Kagawa, J. P. Malerich, V. H. Rawal, Org. Lett. 2008, 10, 2381;
49. Y. Liu, H. Du, Org. Lett. 2013, 15, 740.
50. M. Bandini, A. Eichholzer, Angew. Chem. Int. Ed. 2009, 48, 9533;
51. Angew. Chem. 2009, 121, 9697;
52. M. Bandini, A. Bottoni, M. Chiarucci, G. Cera, G. P. Miscione, J. Am. Chem. Soc. 2012, 134, 20690;
53. Y. Liu, W. Xu, X. Wang, Org. Lett. 2010, 12, 1448.
54. K. Onitsuka, C. Kameyama, H. Sasai, Chem. Lett. 2009, 38, 444;
55. B. Sundararaju, M. Achard, B. Demerseman, L. Toupet, G. V. M. Sharma, C. Bruneau, Angew. Chem. Int. Ed. 2010, 49, 2782;
56. Angew. Chem. 2010, 122, 2842;
57. X. Zhang, W.-B. Liu, Q.-F. Wu, S.-L. You, Org. Lett. 2013, 15, 3746;
58. Z.-P. Yang, C. Liu, S.-L. You, Chem. Sci. 2013, 4, 3239.
59. W.-B. Liu, H. He, L.-X. Dai, S.-L. You, Org. Lett. 2008, 10, 1815;
60. Q.-F. Wu, H. He, W.-B. Liu, S.-L. You, J. Am. Chem. Soc. 2010, 132, 11418;
61. Q.-F. Wu, C. Zheng, S.-L. You, Angew. Chem. Int. Ed. 2012, 51, 1680;
62. Angew. Chem. 2012, 124, 1712;
63. C.-X. Zhuo, Q.-F. Wu, Q. Zhao, Q.-L. Xu, S.-L. You, J. Am. Chem. Soc. 2013, 135, 8169;
64. Q.-L. Xu, C.-X. Zhuo, L.-X. Dai, S.-L. You, Org. Lett. 2013, 15, 5909;
65. X. Zhang, L. Han, S.-L. You, Chem. Sci. 2014, 5, 1059;
66. X. Zhang, W.-B. Liu, H.-F. Tu, S.-L. You, Chem. Sci. 2015, 6, 4525.
67. For a review, see:, M. Bandini, A. Eichholzer, Angew. Chem. Int. Ed. 2009, 48, 9608;
68. Angew. Chem. 2009, 121, 9786.
69. M. A. Schafroth, D. Sarlah, S. Krautwald, E. M. Carreira, J. Am. Chem. Soc. 2012, 134, 20276;
70. O. F. Jeker, A. G. Kravina, E. M. Carreira, Angew. Chem. Int. Ed. 2013, 52, 12166;
71. Angew. Chem. 2013, 125, 12388;
72. J. Deng, R. Li, Y. Luo, J. Li, S. Zhou, Y. Li, J. Hu, A. Li, Org. Lett. 2013, 15, 2022;
73. J. Deng, S. Zhou, W. Zhang, J. Li, R. Li, A. Li, J. Am. Chem. Soc. 2014, 136, 8185;
74. S. Zhou, H. Chen, Y. Luo, W. Zhang, A. Li, Angew. Chem. Int. Ed. 2015, 54, 6878;
75. Angew. Chem. 2015, 127, 6982.
76. For a review on chiral olefins as steering ligands in asymmetric catalysis, see:, C. Defieber, H. Grützmacher, E. M. Carreira, Angew. Chem. Int. Ed. 2008, 47, 4482;
77. Angew. Chem. 2008, 120, 4558.
78. L. Jiao, T. Bach, J. Am. Chem. Soc. 2011, 133, 12990, and references therein;
79. L. Jiao, E. Herdtweck, T. Bach, J. Am. Chem. Soc. 2012, 134, 14563.
80. M. Roggen, E. M. Carreira, J. Am. Chem. Soc. 2010, 132, 11917;
81. M. Lafrance, M. Roggen, E. M. Carreira, Angew. Chem. Int. Ed. 2012, 51, 3470;
82. Angew. Chem. 2012, 124, 3527;
83. L. M. Stanley, J. F. Hartwig, Angew. Chem. Int. Ed. 2009, 48, 7841;
84. Angew. Chem. 2009, 121, 7981.
85. V. Van Rheenen, Tetrahedron Lett. 1969, 10, 985.
86. H. Staudinger, J. Meyer, Helv. Chim. Acta 1919, 2, 635.
87. G. Sirasani, R. B. Andrade, Org. Lett. 2011, 13, 4736.
88. D. Solé, Y. Cancho, A. Llebaria, J. M. Moretó, A. Delgado, J. Am. Chem. Soc. 1994, 116, 12133;
89. J. Bonjoch, D. Solé, J. Bosch, J. Am. Chem. Soc. 1995, 117, 11017;
90. D. Solé, J. Bonjoch, J. Bosch, J. Org. Chem. 1996, 61, 4194;
91. J. Bonjoch, D. Solé, S. Garcia-Rubio, J. Bosch, J. Am. Chem. Soc. 1997, 119, 7230;
92. J. Ma, W. Yin, H. Zhou, J. M. Cook, Org. Lett. 2007, 9, 3491;
93. F. Yu, B. Cheng, H. Zhai, Org. Lett. 2011, 13, 5782.