Asymmetric total synthesis of mycoleptodiscin A

Angewandte Chemie - International Edition

Volumn 54, Issue 23, 2015, Pages 6878-6882

  Zhou, Shupeng ^a   Chen, Hao ^a   Luo, Yijie ^a   Zhang, Wenhao ^a   Li, Ang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

allylic substitution; C N bond formation; indole terpenoids; iridium catalysis; polyene cyclization

Indexed keywords

CATALYSIS; IRIDIUM; ORGANIC COMPOUNDS; POLYCYCLIC AROMATIC HYDROCARBONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALLYLIC SUBSTITUTION; ASYMMETRIC TOTAL SYNTHESIS; BENZOQUINONES; C-N BOND FORMATIONS; ENANTIOSELECTIVE; IRIDIUM CATALYSIS; TERPENOIDS; TOTAL SYNTHESIS;

CYCLIZATION;

ALKALOID; MYCOLEPTODISCIN A;

CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKALOIDS; CYCLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 84930208819     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201501021     Document Type: Article

References (101)

1. I. S. Marcos, R. F. Moro, I. Costales, P. Basabe, D. Díez, Nat. Prod. Rep. 2013, 30, 1509
2. E. J. Velthuisen, S. J. Danishefsky, J. Am. Chem. Soc. 2007, 129, 10640
3. I. S. Marcos, R. F. Moro, I. P. Costales, P. Basabe, D. Díez, F. Mollinedo, J. G. Urones, Tetrahedron 2012, 68, 7932
4. I. S. Marcos, R. F. Moro, I. Costales, P. Basabe, D. Díez, F. Mollinedo, J. G. Urones, Tetrahedron 2013, 69, 7285
5. A. Asanuma, M. Enomoto, T. Nagasawa, S. Kuwahara, Tetrahedron Lett. 2013, 54, 4561
6. B. R. Rosen, E. W. Werner, A. G. O'Brien, P. S. Baran, J. Am. Chem. Soc. 2014, 136, 5571
7. Y. Sun, R. Li, W. Zhang, A. Li, Angew. Chem. Int. Ed. 2013, 52, 9201
8. Angew. Chem. 2013, 125, 9371
9. Y. Sun, P. Chen, D. Zhang, M. Baunach, C. Hertweck, A. Li, Angew. Chem. Int. Ed. 2014, 53, 9012
10. Angew. Chem. 2014, 126, 9158
11. Z. Meng, H. Yu, L. Li, W. Tao, H. Chen, M. Wan, P. Yang, D. J. Edmonds, J. Zhong, A. Li, Nat. Commun. 2015, 6, 6096.
12. Z. Lu, M. Yang, P. Chen, X. C. Xiong, A. Li, Angew. Chem. Int. Ed. 2014, 53, 13840
13. Angew. Chem. 2014, 126, 14060
14. S. Zhou, D. Zhang, Y. Sun, R. Li, W. Zhang, A. Li, Adv. Synth. Catal. 2014, 356, 2867
15. X. Xiong, D. Zhang, J. Li, Y. Sun, S. Zhou, M. Yang, H. Shao, A. Li, Chem. Asian J. 2015, 10, 869.
16. "Terpene Indole Alkaloid Biosynthesis":, S. E. O'Connor, E. McCoy, in Recent Advances in Phytochemistry, Vol. 40 (Eds.:, J. T. Romeo,), Elsevier, Amsterdam, 2006, pp. 1-22
17. M. Baunach, J. Franke, C. Hertweck, Angew. Chem. Int. Ed. 2015, 54, 2604
18. Angew. Chem. 2015, 127, 2640
19. Z. Xu, M. Baunach, L. Ding, C. Hertweck, Angew. Chem. Int. Ed. 2012, 51, 10293
20. Angew. Chem. 2012, 124, 10439
21. M. Baunach, L. Ding, T. Bruhn, G. Bringmann, C. Hertweck, Angew. Chem. Int. Ed. 2013, 52, 9040
22. Angew. Chem. 2013, 125, 9210
23. H. Li, Q. Zhang, S. Li, Y. Zhu, G. Zhang, H. Zhang, X. Tian, S, Zhang, J. Ju, C. Zhang, J. Am. Chem. Soc. 2012, 134, 8996
24. Q. Zhang, H. Li, S. Li, Y. Zhu, G. Zhang, H. Zhang, W. Zhang, R. Shi, C. Zhang, Org. Lett. 2012, 14, 6142
25. H. Li, Y. Sun, Q. Zhang, Y. Zhu, S.-M. Li, A. Li, C. Zhang, Org. Lett. 2015, 17, 306.
26. H. E. Ortega, P. R. Graupner, Y. Asai, K. Tendyke, D. Qiu, Y. Shen, N. Rios, A. E. Arnold, P. D. Coley, T. A. Kursar, W. H. Gerwick, L. Cubilla-Rios, J. Nat. Prod. 2013, 76, 741.
27. R. E. Moore, C. Cheuk, X. G. Yang, G. M. L. Patterson, R. Bonjouklian, T. A. Smitka, J. S. Mynderse, R. S. Foster, N. D. Jones, J. K. Swartzendruber, J. B. Deeter, J. Org. Chem. 1987, 52, 1036.
28. M. Ooike, K. Nozawa, S. Udagawa, K. Kawai, Chem. Pharm. Bull. 1997, 45, 1694.
29. P. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404
30. T. J. Maimone, Y. Ishihara, P. S. Baran, Tetrahedron 2015, DOI:.
31. J. Bonjoch, F. Boncompte, N. Casamitjana, J. Bosch, Tetrahedron 1986, 42, 6693.
32. Z. Lu, Y. Li, J. Deng, A. Li, Nat. Chem. 2013, 5, 679
33. M. Yang, J. Li, A. Li, Nat. Commun. 2015, 6, 6445
34. J. Li, P. Yang, M. Yao, J. Deng, A. Li, J. Am. Chem. Soc. 2014, 136, 16477
35. J. Deng, R. Li, Y. Luo, J. Li, S. Zhou, Y. Li, J. Hu, A. Li, Org. Lett. 2013, 15, 2022
36. M. Wan, M. Yao, J. Gong, P. Yang, H. Liu, A. Li, Chin. Chem. Lett. 2015, 26, 272.
37. M. A. Schafroth, D. Sarlah, S. Krautwald, E. M. Carreira, J. Am. Chem. Soc. 2012, 134, 20276.
38. C. Defieber, M. A. Ariger, P. Moriel, E. M. Carreira, Angew. Chem. Int. Ed. 2007, 46, 3139
39. Angew. Chem. 2007, 119, 3200
40. M. Lafrance, M. Roggen, E. M. Carreira, Angew. Chem. Int. Ed. 2012, 51, 3470
41. Angew. Chem. 2012, 124, 3527
42. M. Roggen, E. M. Carreira, Angew. Chem. Int. Ed. 2012, 51, 8652
43. Angew. Chem. 2012, 124, 8780
44. S. Krautwald, D. Sarlah, M. A. Schafroth, E. M. Carreira, Science 2013, 340, 1065
45. J. Y. Hamilton, D. Sarlah, E. M. Carreira, J. Am. Chem. Soc. 2013, 135, 994
46. J. Y. Hamilton, D. Sarlah, E. M. Carreira, Angew. Chem. Int. Ed. 2013, 52, 7532
47. Angew. Chem. 2013, 125, 7680
48. O. F. Jeker, A. G. Kravina, E. M. Carreira, Angew. Chem. Int. Ed. 2013, 52, 12166
49. Angew. Chem. 2013, 125, 12388
50. J. Y. Hamilton, D. Sarlah, E. M. Carreira, J. Am. Chem. Soc. 2014, 136, 3006
51. S. Krautwald, M. Schafroth, A. D. Sarlah, E. M. Carreira, J. Am. Chem. Soc. 2014, 136, 3020
52. M. A. Schafroth, G. Zuccarello, S. Krautwald, D. Sarlah, E. M. Carreira, Angew. Chem. Int. Ed. 2014, 53, 13898
53. Angew. Chem. 2014, 126, 14118.
54. J. P. Janssen, G. Helmchen, Tetrahedron Lett. 1997, 38, 8025
55. G. Lipowsky, N. Miller, G. Helmchen, Angew. Chem. Int. Ed. 2004, 43, 4595
56. Angew. Chem. 2004, 116, 4695
57. M. Schelwies, P. Dübon, G. Helmchen, Angew. Chem. Int. Ed. 2006, 45, 2466
58. Angew. Chem. 2006, 118, 2526
59. S. Spiess, C. Welter, G. Franck, J. P. Taquet, G. Helmchen, Angew. Chem. Int. Ed. 2008, 47, 7652
60. Angew. Chem. 2008, 120, 7764
61. "Iridium-Catalyzed Asymmetric Allylic Substitutions":, G. Helmchen, in Iridium Complexes in Organic Synthesis (Eds.:, L. A. Oro, C. Claver,), Wiley-VCH, Weinheim, 2009, pp. 211-250
62. "Enantioselective Allylic Substitutions with Carbon Nucleophiles":, S. Förster, G. Helmchen, U. Kazmaier, in Catalytic Asymmetric Synthesis, 3 rd ed., (Eds.: I. Ojima,), Wiley, Hoboken, 2010, pp. 497-641
63. T. Graening, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 17192
64. D. J. Weix, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 7720
65. J. F. Hartwig, L. M. Stanley, Acc. Chem. Res. 2010, 43, 1461
66. W. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 15249
67. W. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 2068
68. M. Chen, J. F. Hartwig, Angew. Chem. Int. Ed. 2014, 53, 12172
69. Angew. Chem. 2014, 126, 12368
70. K. Ye, H. He, W. Liu, L. Dai, G. Helmchen, S, You, J. Am. Chem. Soc. 2011, 133, 19006
71. W. Liu, C. Zheng, C. Zhuo, L. Dai, S. You, J. Am. Chem. Soc. 2012, 134, 4812
72. W. Liu, C. M. Reeves, S. C. Virgil, B. M. Stoltz, J. Am. Chem. Soc. 2013, 135, 10626
73. W. Liu, C. M. Reeves, B. M. Stoltz, J. Am. Chem. Soc. 2013, 135, 17298.
74. J. Deng, S. Zhou, W. Zhang, J. Li, R. Li, A. Li, J. Am. Chem. Soc. 2014, 136, 8185.
75. B. M. Trost, H. C. Arndt, P. E. Strege, T. R. Verhoeven, Tetrahedron Lett. 1976, 17, 3477
76. K. Surendra, G. Rajendar, E. J. Corey, J. Am. Chem. Soc. 2014, 136, 642.
77. S. Yildizhan, J. van Loon, A. Sramkova, M. Ayasse, C. Arsene, C. ten Broeke, S. Schulz, ChemBioChem 2009, 10, 1666.
78. CCDC 1045104 (6) and 1045105 (18) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
79. M. Huang, J. Am. Chem. Soc. 1946, 68, 2487.
80. W. G. Salmond, M. A. Barta, J. L. Havens, J. Org. Chem. 1978, 43, 2057.
81. M. Yasuda, T. Saito, M. Ueba, A. Baba, Angew. Chem. Int. Ed. 2004, 43, 1414
82. Angew. Chem. 2004, 116, 1438
83. T. Saito, Y. Nishimoto, M. Yasuda, A. Baba, J. Org. Chem. 2006, 71, 8516.
84. J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534
85. D. S. Surry, S. L. Buchwald, Angew. Chem. Int. Ed. 2008, 47, 6338
86. Angew. Chem. 2008, 120, 6438.
87. S. Shekhar, T. B. Dunn, B. J. Kotecki, D. K. Montavon, S. C. Cullen, J. Org. Chem. 2011, 76, 4552.
88. D. Ma, Y. Zhang, J. Yao, S. Wu, F. Tao, J. Am. Chem. Soc. 1998, 120, 12459
89. A. Kiyomori, J. F. Marcoux, S. L. Buchwald, Tetrahedron Lett. 1999, 40, 2657
90. A. Klapars, J. C. Antilla, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727
91. D. Ma, Q. Cai, Acc. Chem. Res. 2008, 41, 1450.
92. D. Ma, C. Xia, J. Jiang, J. Zhang, Org. Lett. 2001, 3, 2189
93. A. Fürstner, V. Mamane, Chem. Commun. 2003, 2112
94. K. Yamada, T. Kurokawa, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2003, 125, 6630
95. K. Okano, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2006, 128, 7136
96. K. Okano, H. Tokuyama, T. Fukuyama, Chem. Asian J. 2008, 3, 296
97. K. Okano, H. Fujiwara, T. Noji, T. Fukuyama, H. Tokuyama, Angew. Chem. Int. Ed. 2010, 49, 5925
98. Angew. Chem. 2010, 122, 6061
99. H. Tokuyama, K. Okano, H. Fujiwara, T. Noji, T. Fukuyama, Chem. Asian J. 2011, 6, 560.
100. K. Yamada, T. Kubo, H. Tokuyama, T. Fukuyama, Synlett 2002, 231
101. M. Pineschi, F. Bertolini, P. Crotti, F. Macchia, Org. Lett. 2006, 8, 2627.