Reagent control of [1,2]-Wagner-Meerwein shift chemoselectivity following the nazarov cyclization: Application to the total synthesis of enokipodin B

Chemistry - A European Journal

Volumn 19, Issue 15, 2013, Pages 4835-4841

  Lebœuf, David ^a   Wright, Christopher M ^a   Frontier, Alison J ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

copper; cyclization; rearrangement; sesquiterpenes; total synthesis

Indexed keywords

CARBON FRAMEWORK; CHEMO-SELECTIVITY; COPPER COMPLEXES; LIGAND ARCHITECTURE; NAZAROV CYCLIZATION; REARRANGEMENT; SESQUITERPENES; TOTAL SYNTHESIS;

CATIONIC POLYMERIZATION; COPPER; OLEFINS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

COPPER; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ENOKIPODIN B; LIGAND; SESQUITERPENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COPPER; CYCLIZATION; INDICATORS AND REAGENTS; LIGANDS; MOLECULAR STRUCTURE; SESQUITERPENES; STEREOISOMERISM;

EID: 84875864923     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203395     Document Type: Article

References (110)

1. C. Santelli-Rouvier, M. Santelli, Synthesis 1983, 429.
2. K. L. Habermas, S. E. Denmark, T. K. Jones in Organic Reactions, Vol. 45, (Ed.: L. A. Paquette, L. A.), John Wiley & Sons, New York, 1994, pp. 1-158
3. M. Harmata, Chemtracts 2004, 17, 416
4. H. Pellissier, Tetrahedron 2005, 61, 6479
5. A. J. Frontier, C. Collison, Tetrahedron 2005, 61, 7577
6. M. A. Tius, Eur. J. Org. Chem. 2005, 2193
7. W. Nakanishi, F. G. West, Curr. Opin. Drug Discov. Devel. 2009, 12, 732
8. T. Vaidya, R. Eisenberg, A. J. Frontier, ChemCatChem 2011, 3, 1531.
9. For recent examples of Nazarov cyclizations, see: a) D. R. Williams, L. A. Robinson, C. R. Nevill, J. P. Reddy, Angew. Chem. 2007, 119, 933
10. Angew. Chem. Int. Ed. 2007, 46, 915
11. W. He, J. Huang, X. Sun, A. J. Frontier, J. Am. Chem. Soc. 2008, 130, 300
12. A. P. Marcus, A. S. Lee, R. L. Davis, D. J. Tantillo, R. Sarpong, Angew. Chem. 2008, 120, 6479
13. Angew. Chem. Int. Ed. 2008, 47, 6379
14. A. Y. Bitar, A. J. Frontier, Org. Lett. 2009, 11, 49
15. C. J. Rieder, K. J. Winberg, F. G. West, J. Am. Chem. Soc. 2009, 131, 7504
16. J. A. Malona, K. Cariou, A. J. Frontier, J. Am. Chem. Soc. 2009, 131, 7560
17. R. Singh, M. K. Parai, G. Panda, Org. Biomol. Chem. 2009, 7, 1858
18. P. Cordier, C. Aubert, M. Malacria, E. Lac-te, V. Gandon, Angew. Chem. 2009, 121, 8913
19. Angew. Chem. Int. Ed. 2009, 48, 8757
20. M. Wang, F. Han, H. Yuan, Q. Liu, Chem. Commun. 2010, 46, 2247
21. P. A. Wender, R. T. Stemmler, L. E. Sirois, J. Am. Chem. Soc. 2010, 132, 2532
22. K. Murugan, S. Srimurugan, C. Chen, Chem. Commun. 2010, 46, 1127
23. T. Vaidya, A. C. Atesin, I. R. Herrick, A. J. Frontier, R. Eisenberg, Angew. Chem.
24. Angew. Chem. Int. Ed. 2010, 49, 3363
25. D. J. Kerr, J. M. White, B. L. Flynn, J. Org. Chem. 2010, 75, 7073
26. A. P. Marcus, R. Sarpong, Org. Lett. 2010, 12, 4560
27. Z. Cai, M. Harmata, Org. Lett. 2010, 12, 5668
28. C. J. Hastings, M. D. Pluth, R. G. Bergman, K. N. Raymond, J. Am. Chem. Soc. 2010, 132, 6938
29. C. J. Rieder, K. J. Winberg, F. G. West, J. Org. Chem. 2011, 76, 50
30. W. T. Spencer, III, M. D. Levin, A. J. Frontier, Org. Lett. 2011, 13, 414
31. W.-D. Z. Li, W. G. Duo, C. H. Zhang, Org. Lett. 2011, 13, 3538
32. M. E. Krafft, D. V. Vidhani, J. W. Cran, M. Manoharan, Chem. Commun. 2011, 47, 6707
33. J. A. Malona, K. Cariou, W. T. Spencer, III, A. J. Frontier, J. Org. Chem. 2012, 77, 1891
34. P. Magnus, W. A. Freund, E. J. Moorhead, T. Rainey, J. Am. Chem. Soc. 2012, 134, 6140
35. D. J. Kerr, M. Miletic, J. H. Chaplin, J. M. White, B. L. Flynn, Org. Lett. 2012, 14, 1732
36. D. J. Kerr, B. L. Flynn, Org. Lett. 2012, 14, 1740
37. N. Shimada, C. Stewart, W. F. Bow, A. Jolit, K. Wong, Z. Zhou, M. A. Tius, Angew. Chem. 2012, 124, 5825
38. Angew. Chem. Int. Ed.(2012), 51, 5727
39. Y.-K. Wu, T. Niu, F. G. West, Chem. Commun. 2012, 48, 9186.
40. For review, see a) T. N. Grant, C. J. Rieder, F. G. West, Chem.
41. M. Janka, W. He, I. E. Haedicke, F. R. Fronczek, A. J. Frontier, R. Eisenberg, J. Am. Chem. Soc. 2006, 128, 5312;
42. F. Dhoro, T. E. Kristensen, V. Stockmann, G. P. A. Yap, M. A. Tius, J. Am. Chem. Soc. 2007, 129, 7256
43. J. Nie, H. W. Zhu, H. F. Cui, M. Q. Hua, J. A. Ma, Org. Lett. 2007, 9, 3053
44. V. M. Marx, D. J. Burnell, Org. Lett. 2009, 11, 1229
45. M. Fujiwara, M. Kawatsura, S. Hayase, M. Nanjo, T. Itoh, Adv. Synth. Catal. 2009, 351, 123;
46. V. M. Marx, T. S. Cameron, D. J. Burnell, Tetrahedron Lett. 2009
47. V. M. Marx, D. J. Burnell, J. Am. Chem. Soc. 2010, 132, 1685
48. C. J. Rieder, R. J. Fradette, F. G. West, Heterocycles 2010, 80, 1413
49. O. Scadeng, F. G. West, Org. Lett. 2011, 13, 114
50. V. M.Marx, F. M. LeFort, D. J. Burnell, Adv. Synth. Catal. 2011, 353, 64;
51. Y.-K. Wu, R. McDonald, F. G. West, Org. Lett. 2011, 13, 3584;
52. V. M. Marx, R. L. Stoddard, G. S. Heverly-Coulson, D. J. Burnell, Chem. Eur. J. 2011, 17, 8098
53. M. Rueping, W. Ieawsuwan, Chem. Commun. 2011, 47, 11450.
54. L. Zhang, S. Wang, J. Am. Chem. Soc. 2006, 128, 1442
55. G. Lemi-re, V. Gandon, K. Cariou, A. Hours, T. Fukuyama, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2009, 131, 2993
56. H. Zheng, X. Xie, J. Yang, C. Zhao, P. Jing, B. Fang, X. She, Org. Biomol. Chem. 2011, 9, 7555.
57. T. N. Grant, F. G. West, Org. Lett. 2007, 9, 3789.
58. J. L. Brooks, P. Caruana, A. J. Frontier, J. Am. Chem. Soc. 2011, 133, 12454.
59. J. Huang, A. J. Frontier, J. Am. Chem. Soc. 2007, 129, 8060
60. J. Huang, D. Leboeuf, A. J. Frontier, J. Am. Chem. Soc. 2011, 133, 6307
61. D. Leboeuf, J. Huang, V. Gandon, A. J. Frontier, Angew. Chem. 2011, 123, 11173
62. Angew. Chem. Int. Ed. 2011, 50, 10981
63. D. Leboeuf, V. Gandon, J. Ciesielski, A. J. Frontier, J. Am. Chem. Soc. 2012, 134, 6296.
64. For other examples, see: a) G. Ohloff, K. H. Schulte-Elte, E. Demole, Helv. Chim. Acta 1971, 54, 2913
65. L. A. Paquette, W. E. Fristad, D. S. Dime, T. R. Bailey, J. Org. Chem. 1980, 45, 3017
66. S. E. Denmark, G. A. G. Hite, Helv. Chim. Acta 1988, 71, 195.
67. A. G. Gruhn, W. Reusch, Tetrahedron 1993, 49, 8159
68. C. Kuroda, H. Koshio, A. Koito, H. Sumiya, A. Murase, Y. Hirono, Tetrahedron 2000, 56, 6441
69. P. Chiu, S. L. Li, Org. Lett. 2004, 6, 613.
70. W. He, I. R. Herrick, T. A. Atesin, P. A. Caruana, C. A. Kellenberger, A. J. Frontier, J. Am. Chem. Soc. 2008, 130, 1003.
71. G. Liang, S. N. Gradl, D. Trauner, Org. Lett. 2003, 5, 4931;
72. V. K. Aggarwal, A. J. Belfield, Org. Lett. 2003, 5, 5075.
73. For other examples of asymmetric Nazarov cyclizations, see: a) G.
74. M. Rueping, W. Ieawsuwan, A. P. Antonchick, B. J. Nachtsheim, Angew. Chem. 2007, 119, 2143
75. Angew. Chem. Int. Ed. 2007, 46, 2097
76. A. R. Banaag, M. A. Tius, J. Org. Chem. 2008, 73, 8133
77. I. Walz, A. Togni, Chem. Commun. 2008, 4315
78. M. Rueping, W. Ieawsuwan, Adv. Synth. Catal. 2009, 351, 78
79. K. Yaji, M. Shindo, Synlett 2009, 2524
80. P. Cao, C. Deng, Y.-Y. Zhou, X.-L. Sun, J.-C. Zheng, W. Xie, Y. Tang, Angew. Chem. 2010, 122, 4565
81. Angew. Chem. Int. Ed. 2010, 49, 4463
82. W. F. Bow, A. K. Basak, A. Jolit, D. A. Vicic, M. A. Tius, Org. Lett. 2010, 12, 440
83. A. K. Basak, N. Shimada, W. F. Bow, D. A. Vicic, M. A. Tius, J. Am. Chem. Soc. 2010, 132, 8266
84. S. Raja, W. Ieawsuwan, V. Korotkov, M. Rueping, Chem. Asian J. 2012, 7, 2361.
85. N. K. Ishikawa, K. Yamaji, S. Tahara, Y. Fukushi, K. Takahashi, Phytochemistry 2000, 54, 777
86. N. K. Ishikawa, Y. Fukushi, K. Yamaji, S. Tahara, K. Takahashi, J. Nat. Prod. 2001, 64, 932.
87. For recent syntheses, see: a) A. Abad, C. Agull-, M. Arn-, A. C.
88. C. Fuganti, S. Serra, J. Org. Chem. 1999, 64, 8728
89. T. Cohen, T. Kreethadumrongdat, X. Liu, V. Kulkarni, J. Am. Chem. Soc. 2001, 123, 3478
90. R. S. Grainger, A. Patel, Chem. Commun. 2003, 1072
91. A. Nayek, M. G. B. Drew, S. Ghosh, Tetrahedron 2003, 59, 5175.
92. J. Gagnepain, F. Castet, S. Quideau, Angew. Chem. 2007, 119, 1555;
93. For recent syntheses, see: a) A. Abad, C. Agull-, A. C. CuÇat, R. H.
94. P. D. Gupta, A. Pal, A. Roy, D. Mukherjee, Tetrahedron Lett. 2000, 41, 7563
95. A. Srikrishna, M. S. Rao, Synlett 2002, 0340
96. A. Srikrishna, G. Satyanarayana, Tetrahedron Lett. 2003, 44, 1027
97. A. M. Bernard, A. Frongia, F. Secci, P. P. Piras, Chem. Commun. 2005, 3853.
98. T. Paul, A. Pal, P. D. Gupta, D. Mukherjee, Tetrahedron Lett. 2003, 44, 737
99. S. P. Chavan, R. K. Kharul, R. R. Kale, D. A. Khobragade, Tetrahedron 2003, 59, 2737
100. S. P. Chavan, M. Thakkar, R. K. Kharul, A. B. Pathak, G. V. Bhosekar, M. M. Bhadbhade, Tetrahedron 2005, 61, 3873.
101. A. Srikrishna, P. C. Ravikumar, Synthesis 2007, 65.
102. A. Srikrishna, M. S. Rao, Synlett 2004, 0374
103. S. Kuwahara, M. Saito, Tetrahedron Lett. 2004, 45, 5047
104. M. Saito, S. Kuwahara, Biosci. Biotechnol. Biochem. 2005, 69, 374
105. F. Secci, A. Frongia, J. Ollivier, P. P. Piras, Synthesis 2007, 999
106. M. Yoshida, Y. Shoji, K. Shishido, Org. Lett. 2009, 11, 1441
107. J. A. Luj-n-Montelongo, J. G. Avila-Z-rraga, Tetrahedron Lett. 2010, 51, 2232.
108. V. B. Rao, S. Wolff, W. C. Agosta, Tetrahedron 1986, 42, 1549.
109. E. Alvarez-Manzaneda, R. Chahboun, E. Cabrera, E. Alvarez, A., hem. Commun.(2009) 592.
110. A. Srikrishna, G. Satyanarayana, Synth. Commun. 2004, 34, 3847.