Directed metalationcross-coupling strategies. Total syntheses of the alleged and the revised phenanthrene natural product gymnopusin

Helvetica Chimica Acta

Volumn 95, Issue 12, 2012, Pages 2680-2694

  Wang, Xin ^a,b   Fu, Jian Min ^a,c   Snieckus, Victor ^a,d  

^a UNIVERSITY OF WATERLOO   (Canada)

^b ISIS PHARMACEUTICALS   (United States)

^c Pharmaron Beijing Co Ltd   (China)

^d QUEEN S UNIVERSITY   (Canada)

Author keywords

Cross coupling reactions; Fries rearrangement; Gymnopusin; Metalation; Suzuki Miyaura reactions

Indexed keywords

REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

CROSS COUPLING REACTIONS; DIRECTED ORTHO METALATION; FRIES REARRANGEMENT; GYMNOPUSIN; METALATIONS; NATURAL PRODUCTS; POLYCYCLIC AROMATICS; REGIO-SELECTIVE;

METALS;

PHENANTHRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLIZATION; DESILYLATION; HALOGENATION; METALATION; PRIORITY JOURNAL; SILYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84872860252     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201200564     Document Type: Article

References (129)

1. W. Xue, D. Warshawsky, Toxicol. Appl. Pharmacol. 2005, 206, 73
2. A. Dipple, R. C. Moschel, C. A. H. Bigger, in 'Chemical Carcinogenesis', 2nd edn., Ed. C.E. Searle, ACS Monograph 182, American Chemical Society, Washington, D.C., 1984, Vol.1, p.41.
3. S. Fallahtafti, T. Rantanen, R. S. Brown, V. Snieckus, P. V. Hodson, Aquat. Toxicol. 2012, 106-107, 56
4. C. J. Martyniuk, B. C. Sanchez, N. J. Szabo, N. D. Denslow, M. S. Sepúlveda, Aquat. Toxicol. 2009, 95, 1
5. R. Munoz, B. Guieysse, B. Mattiasson, Appl. Microbiol. Biotechnol. 2003, 61, 261
6. R. vanHerwijnen, P. Wattiau, L. Bastiaens, L. Daal, L. Jonker, D. Springael, H. A. J. Govers, J. R. Parson, Res. Microbiol. 2003, 154, 199
7. W. R. Reeves, R. Barhounmi, R. C. Burgharat, S. L. Lemke, K. Mayura, T. T. McDonald, T. D. Philips, K. C. Donnelly, Environ. Sci. Technol. 2001, 35, 1630
8. N. Basu, S. Billiard, N. Fragoso, A. Omoike, S. Tabash, P. Hodson, Environ. Toxicol. Chem. 2001, 20, 1244.
9. A. R. Diercks, R. C. Highsmith, V. I. Asper, D. Joung, Z. Zhou, L. Guo, A. M. Shiller, S. B. Joye, A. P. Teske, N. Guinasso, T. L. Wade, S. E. Lohrenz, Geophys. Res. Lett. 2010, 37, L20602
10. P. V. Hodson, K. Qureshi, C. A. J. Noble, P. Akhtar, R. S. Brown, Aquat. Toxicol. 2007, 81, 275.
11. N. Grova, C. Feidt, F. Monteau, B. LeBizec, G. Rychen, Polycyclic Aromat. Compd. 2008, 28, 98.
12. A. Kovács, A. Vasas, J. Hohmann, Phytochemistry 2008, 69, 1084.
13. V. Kumar, Poonam, A. K. Prasad, V. S. Parmar, Nat. Prod. Rep. 2003, 20, 565
14. Z.Li, Z. Jin, R. Huang, Synthesis 2001, 2365
15. S. Kim, Y. M. Lee, J. Lee, T. Lee, Y. Fu, Y. Song, J. Cho, D. Kim, J. Org. Chem. 2007, 72, 4886
16. J. P. Michael, Nat. Prod. Rep. 2008, 25, 139, and previous reports in this series.
17. D.-J. Ding, X.-Y. Cao, F. Dai, X.-Z. Li, G.-Y. Liu, D. Lin, X. Fu, X.-L. Jin, B. Zhou, Food Chem. 2012, 135, 1011
18. K. Wang, Y. Hu, Y. Liu, N. Mi, Z. Fan, Y. Liu, Q. Wang, J. Agric. Food Chem. 2010, 58, 12337
19. X. Yang, Q. Shi, Y.-N. Liu, G. Zhao, K. F. Bastow, J.-C. Lin, S.-C. Yang, P.-C. Yang, K.-H. Lee, J. Med. Chem. 2009, 52, 5262
20. L. Wei, Q. Shi, K. F. Bastow, A. Brossi, S. L. Morris-Natschke, K. Nakagawa-Goto, T.-S. Wu, S.-L. Pan, C.-M. Teng, K.-H. Lee, J. Med. Chem. 2007, 50, 3674
21. J. M. Schmidt, J. Mercure, G. B. Tremblay, M. Pagé, A. Kalbakji, M. Feher, R. Dunn-Dufault, M. G. Peter, P. R. Redden, J. Med. Chem. 2003, 46, 1408
22. H. Komatsu, M. Watanabe, M. Ohyama, T. Enya, K. Koyama, T. Kanazawa, N. Kawahara, T. Sugimura, K. Wakabayashi, J. Med. Chem. 2001, 44, 1833.
23. M. J. Sienkowska, J. M. Farrar, F. Zhang, S. Kusuma, P. A. Heiney, P. Kaszynski, J. Mater. Chem. 2007, 17, 1399
24. A. M. Machado, M. Munaro, T. D. Martins, L. Y. A. Dávila, R. Giro, M. J. Caldas, T. D. Z. Atvars, L. C. Akcelrud, Macromolecules 2006, 39, 3398
25. G. Scherowsky, X. H. Chen, J. Mater. Chem. 1995, 5, 417
26. J. W. Ciszek, J. M. Tour, Tetrahedron Lett. 2004, 45, 2801.
27. A. J. Floyd, S. F. Dyke, S. E. Ward, Chem. Rev. 1976, 76, 509.
28. J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev. 2011, 40, 102
29. S. Lebrun, A. Couture, E. Deniau, P. Grandclaudon, Tetrahedron 1999, 55, 2659
30. P. Hanson, P. W. Lövenich, S. C. Rowell, P. H. Walton, A. W. Timms, J. Chem. Soc., Perkin Trans. 2 1999, 49
31. F. W. Wassmundt, W. F. Kiesman, J. Org. Chem. 1995, 60, 196.
32. K. B. Jørgensen, Molecules 2010, 15, 4334
33. F. B. Mallory, C. Mallory, Org. React. 1984, 30, 1
34. T. Bach, J. Hehn, Angew. Chem., Int. Ed. 2011, 50, 1000
35. A. G. Neo, A. Pérez, C. Lõpez, L. Castedo, G. Tojo, J. Org. Chem. 2009, 74, 3203
36. J. N. Moorthy, P. Venkatakrishnan, S. Sengupta, M. Baidya, Org. Lett. 2006, 8, 4891
37. R. ElAbed, B. BenHassine, J.-P. Genêt, M. Gorsane, A. Marinetti, Eur. J. Org. Chem. 2004, 1517
38. M. C. Pampín, J. C. Estévez, R. J. Estévez, R. Suau, L. Castedo, Tetrahedron 2003, 59, 8057
39. M. C. Pampín, J. C. Estévez, R. J. Estévez, M. Maestro, L. Castedo, Tetrahedron 2003, 59, 7231
40. J. F. Almeida, L. Castedo, D. Fernández, A. G. Neo, V. Romero, G. Tojo, Org. Lett. 2003, 5, 4939.
41. S. Radix, R. Barret, Tetrahedron 2007, 63, 12379
42. D. C. Harrowven, M. I. T. Nunn, D. R. Fenwick, Tetrahedron Lett. 2002, 43, 7345
43. A. Couture, E. Deniau, P. Grandclaudon, C. Hoarau, J. Org. Chem. 1998, 63, 3128.
44. T. N. Barrett, D. C. Braddock, A. Monta, M. R. Webb, J. P. White, J. Nat. Prod. 2011, 74, 1980
45. A. Stoye, T. Opatz, Org. Lett. 2010, 12, 2140
46. W. Zeng, S. R. Chemler, J. Org. Chem. 2008, 73, 6045.
47. H. Li, K.-H. He, J. Liu, B.-Q. Wang, K.-Q. Zhao, P. Hu, Z.-J. Shi, Chem. Commun. 2012, 48, 7028
48. A. Yadav, H. Ila, H. Junjappa, Eur. J. Org. Chem. 2010, 338
49. M. Shimizu, I. Nagao, Y. Tomioka, T. Hiyama, Angew. Chem. 2008, 120, 8216
50. K. Kamikawa, I. Takemoto, S. Takemoto, H. Matsuzaka, J. Org. Chem. 2007, 72, 7406.
51. J. E. McMurray, Chem. Rev. 1989, 89, 1513
52. B. E. Kahn, R. D. Rieke, Chem. Rev. 1988, 88, 733
53. J. E. McMurray, Acc. Chem. Res. 1983, 16, 405
54. Y. Xia, Z. Liu, Q. Xiao, P. Qu, R. Ge, Y. Zhang, J. Wang, Angew. Chem., Int. Ed. 2012, 51, 5714
55. A.-E. Gies, M. Pfeffer, J. Org. Chem. 1999, 64, 3650.
56. S. B. Jones, S. L. Castle, Org. Lett. 2006, 8, 3757
57. A. Iuliano, P. Piccioli, D. Fabbri, Org. Lett. 2004, 6, 3711.
58. F. Ye, Y. Shi, L. Zhou, Q. Xiao, Y. Zhang, J. Wang, Org. Lett. 2011, 13, 5020
59. M. J. Niphakls, G. I. Georg, Org. Lett. 2011, 13, 196
60. A. Li, P. J. Kindelin, D. A. Klumpp, Org. Lett. 2006, 8, 1233
61. A. Fürstner, J. W. J. Kennedy, Chem.-Eur. J. 2006, 12, 7398
62. H.-C. Shen, J.-M. Tang, H.-K. Chang, C.-W. Yang, R.-S. Liu, J. Org. Chem. 2005, 70, 10113
63. W. M. Seganish, P. DeShong, Org. Lett. 2006, 8, 3951
64. T. Yao, M. A. Campo, R. C. Larock, J. Org. Chem. 2005, 70, 3511
65. V. Mamane, P. Hannen, A. Fürstner, Chem.-Eur. J. 2004, 10, 4556
66. T. Yao, M. A. Campo, R. C. Larock, Org. Lett. 2004, 6, 2677
67. A. Fürstner, V. Mamane, Chem. Commun. 2003, 2112.
68. R. Sanz, Org. Prep. Proced. Int. 2008, 40, 215
69. D. Peña, D. Pérez, E. Guitián, L. Castedo, J. Am. Chem. Soc. 1999, 121, 5827
70. D. Peña, D. Pérez, E. Guitián, L. Castedo, J. Org. Chem. 2000, 65, 6944
71. S. A. Worlikar, R. C. Larock, J. Org. Chem. 2009, 74, 9132
72. Z. Liu, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2005, 127, 15716
73. M. Catellani, E. Motti, S. Baratta, Org. Lett. 2001, 3, 3611
74. K.-i. Kanno, Y. Liu, A. Iesato, K. Nakajima, T. Takahashi, Org. Lett. 2005, 7, 5453.
75. Y.-L. Liu, Y. Liang, S.-F. Pi, X.-C. Huang, J.-H. Li, J. Org. Chem. 2009, 74, 3199.
76. A. Matsumoto, L. Ilies, E. Nakamura, J. Am. Chem. Soc. 2011, 133, 6557
77. A. B. Mandal, G.-H. Lee, Y.-H. Liu, S.-M. Peng, M.-k. Leung, J. Org. Chem. 2000, 65, 332.
78. W. Krasodomski, M. K. Łuczyński, J. Wilamowski, J. J. Sepioł, Tetrahedron 2003, 59, 5677.
79. R. Yougnia, C. Rochais, J. Sopkovà-de Oliveira Santos, P. Dallemagne, S. Rault, Tetrahedron 2010, 66, 2803
80. C. Rochais, R. Yougnia, P. Dallemagne, S. Rault, Tetrahedron Lett. 2009, 50, 5704
81. J. K. Kim, Y. H. Kim, H. T. Nam, B. T. Kim, J.-N. Heo, Org. Lett. 2008, 10, 3543
82. Y. H. Kim, H. Lee, Y. J. Kim, B. T. Kim, J.-N. Heo, J. Org. Chem. 2008, 73, 495.
83. S. Menon, D. Sinha-Mahapatra, J. W. Herndon, Tetrahedron 2007, 63, 8788
84. Y. Wang, J. Xu, D. J. Burton, J. Org. Chem. 2006, 71, 7780
85. Y. Zhang, J. W. Herndon, Tetrahedron Lett. 2006, 47, 5303
86. Y. Zhang, J. W. Herndon, Org. Lett. 2003, 5, 2043.
87. V. Snieckus, Chem. Rev. 1990, 90, 879
88. 2-Hybridized Carbon Atoms', in ' Handbook of CH Transformations', Ed. G. Dyker, Wiley-VCH, New York, 2005, p.106
89. C. G. Hartung, V. Snieckus, 'The Directed ortho Metalation Reaction. A Point of Departure for New Synthetic Aromatic Chemistry', in 'Modern Arene Chemistry', Ed. D. Astruc, Wiley-VCH, New York, 2002, p.330
90. J. Clayden, in 'The Chemistry of Organolithium Compounds, Part 2', Eds. Z. Rappoport, I. Marek, Wiley, Chichester, 2004, p.495.
91. E. Anctil, V. Snieckus, in 'Metal-Catalyzed Cross-Coupling Reactions', 2nd edn., Eds. F. Diederich, A. deMeijere, Wiley-VCH, Weinheim, 2004, p.761
92. E. Anctil, V. Snieckus, J. Organomet. Chem. 2002, 653, 150
93. C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot, V. Snieckus, Angew. Chem., Int. Ed. 2012, 51, 5062.
94. M. C. Whisler, S. MacNeil, V. Snieckus, P. Beak, Angew. Chem., Int. Ed. 2004, 43, 2206.
95. F. Gosselin, S. Lau, C. Nadeau, T. Trinh, P. D. O'Shea, I. W. Davies, J. Org. Chem. 2009, 74, 7790
96. X. Cai, S. Brown, P. Hodson, V. Snieckus, Can. J. Chem. 2004, 82, 195
97. J.-M. Fu, V. Snieckus, Can. J. Chem. 2000, 78, 905
98. M. A. F. Brandão, A. B. Oliveira, V. Snieckus, Tetrahedron Lett. 1993, 34, 2437
99. J.-M. Fu, M. Sharp, V. Snieckus, Tetrahedron Lett. 1988, 29, 5459.
100. C. Schneider, E. David, A. Toutov, V. Snieckus, Angew. Chem., Int. Ed. 2012, 51, 2722
101. C. James, A. Coelho, M. Gevaert, P. Forgione, V. Snieckus, J. Org. Chem. 2009, 74, 4094
102. Z. Zhao, A. Jaworski, I. Piel, V. Snieckus, Org. Lett. 2008, 10, 2617
103. S. MacNeil, B. Wilson, V. Snieckus, Org. Lett. 2006, 8, 1133
104. X. Cai, V. Snieckus, Org. Lett. 2004, 6, 2293
105. J. A. McCubbin, X. Tong, R. Wang, Y. Zhao, V. Snieckus, R. P. Lemieux, J. Am. Chem. Soc. 2004, 126, 1161.
106. P. L. Majumder, S. Banerjee, Phytochemistry 1988, 27, 245.
107. A. B. Hughes, M. V. Sargent, J. Chem. Soc., Perkin Trans. 1 1989, 1787.
108. J.-M. Fu, Ph.D. Thesis, University of Waterloo, 1990
109. X. Wang, V. Snieckus, Tetrahedron Lett. 1991, 32, 4879.
110. P. L. Majumder, S. Banerjee, Indian J. Chem., Sect. B 1989, 28, 1085.
111. R. J. Mills, N. J. Taylor, V. Snieckus, J. Org. Chem. 1989, 54, 4372.
112. R. L. Hillard III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058.
113. J.-M. Fu, V. Snieckus, Tetrahedron Lett. 1990, 31, 1665.
114. Y. Hoshino, N. Miyaura, A. Suzuki, Bull. Chem. Soc. Jpn. 1988, 61, 3008.
115. J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162.
116. J. R. Luly, H. Rapoport, J. Org. Chem. 1981, 46, 2745
117. J. Peyton, P. S. Callery, A. T. Shulgin, N. Castagnoli Jr., J. Org. Chem. 1976, 41, 3627.
118. H.-D. Becker, J. Org. Chem. 1965, 30, 982.
119. Y. Tamura, T. Yakura, H. Tohma, K. Kikuchi, Y. Kita, Synthesis 1989, 126.
120. C. D. Snyder, H. Rapoport, J. Am. Chem. Soc. 1972, 94, 227.
121. W. Wang, M.Sc. Thesis, University of Waterloo, 1991
122. W. Wang, V. Snieckus, J. Org. Chem. 1992, 57, 424.
123. M. Sibi, V. Snieckus, J. Org. Chem. 1983, 48, 1935.
124. X. Wang, V. Snieckus, Tetrahedron Lett. 1991, 32, 4883
125. K. Green, J. Org. Chem. 1991, 56, 4325.
126. L. R. Worden, P. J. Smith, G. N. Widiger, J. Chem. Soc. C 1970, 227.
127. D. D. Perrin, W. L. Armarego, D. R. Perrin, 'Purification of Laboratory Chemicals', 2nd edn., Pergamon Press, Oxford, 1980.
128. K. F. Podraza, R. L. Bassfield, J. Org. Chem. 1988, 53, 2643.
129. R. F. Heck, 'Palladium Reagents in Organic Synthesis', Academic, New York, 1985.