Catalytic enantioselective desymmetrisation as a tool for the synthesis of hodgkinsine and hodgkinsine B

Chemistry - A European Journal

Volumn 18, Issue 52, 2012, Pages 16754-16764

  Snell, Robert H ^a   Durbin, Matthew J ^a   Woodward, Robert L ^b   Willis, Michael C ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

alkaloids; desymmetrization; heterocycles; natural products; total synthesis

Indexed keywords

ALKALOIDS; AMINES; CATALYSIS; PALLADIUM;

DESYM-METRIZATION; DIMERIC ALKALOIDS; ENANTIOSELECTIVE; HETEROCYCLES; NATURAL PRODUCTS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

EID: 84872896067     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203150     Document Type: Article

References (93)

1. P. L. Julian, J. Pikl, J. Am. Chem. Soc. 1933, 55, 2105
2. P. L. Julian, J. Pikl, D. Boggess, J. Am. Chem. Soc. 1934, 56, 1797
3. P. L. Julian, J. Pikl, J. Am. Chem. Soc. 1935, 57, 539
4. P. L. Julian, J. Pikl, J. Am. Chem. Soc. 1935, 57, 563
5. P. L. Julian, J. Pikl, J. Am. Chem. Soc. 1935, 57, 755.
6. D. Crich, A. Banerjee, Acc. Chem. Res. 2007, 40, 151.
7. G. A. Cordell, J. E. Saxton, in The Alkaloids, Vol. 20, Elsevier, Amsterdam, 1981, p. 10
8. A. Steven, L. E. Overman, Angew. Chem. 2007, 119, 5584
9. Angew. Chem. Int. Ed. 2007, 46, 5488
10. P. Ruiz-Sanchis, S. A. Savina, F. Albericio, M. Álvarez, Chem. Eur. J. 2011, 17, 1388
11. M. A. Schmidt, M. Movassaghi, Synlett 2008, 313.
12. E. F. L. J. Anet, G. K. Hughes, E. Ritchie, Aust. J. Chem. 1961, 14, 173
13. K. P. Parry, G. F. Smith, J. Chem. Soc. Perkin Trans. 1 1978, 1671
14. T. Tokuyama, J. W. Daly, Tetrahedron 1983, 39, 41
15. L. Verotta, T. Pilati, M. Tatò, E. Elisabetsky, T. A. Amador, D. S. Nunes, J. Nat. Prod. 1998, 61, 392
16. V. Jannic, F. Guéritte, O. Laprévote, L. Serani, M. Martin, T. Sévenet, P. Potier, J. Nat. Prod. 1999, 62, 838
17. L. Verotta, F. Peterlongo, E. Elisabetsky, T. A. Amador, D. S. Nunes, J. Chromatogr. A 1999, 841, 165.
18. H. A. Saad, S. H. El-Sharkawy, W. T. Shier, Planta Med. 1995, 61, 313.
19. Y. Adjibadé, H. Saad, B. Kuballa, J. P. Beck, T. Sévenet, P. Cabalion, R. Anton, J. Ethnopharmacol. 1990, 29, 127.
20. T. A. Amador, L. Verotta, D. S. Nunes, E. Elisabetsky, Planta Med. 2000, 66, 770
21. L. Verotta, F. Orsini, M. Sbacchi, M. A. Scheildler, T. A. Amador, E. Elisabetsky, Bioorg. Med. Chem. 2002, 10, 2133
22. D. D. Porto, A. T. Henriques, A. G. Fett-Neto, Open Bioact. Compd. J. 2009, 2, 29
23. J. Sanz-Biset, J. Campos-de-la-Cruz, M. A. Epiquién-Rivera, S. Caňigueral, J. Ethnopharmacol. 2009, 122, 333.
24. J. T. Link, L. E. Overman, J. Am. Chem. Soc. 1996, 118, 8166
25. L. E. Overman, D. V. Paone, B. A. Stearns, J. Am. Chem. Soc. 1999, 121, 7702
26. J. J. Kodanko, L. E. Overman, Angew. Chem. 2003, 115, 2632
27. Angew. Chem. Int. Ed. 2003, 42, 2528
28. J. J. Kodanko, S. Hiebert, E. A. Peterson, L. Sung, L. E. Overman, V. M. Linck, G. C. Goerck, T. A. Amador, M. B. Leal, E. Elisabetsky, J. Org. Chem. 2007, 72, 7909
29. A. D. Lebsack, J. T. Link, L. E. Overman, B. A. Stearns, J. Am. Chem. Soc. 2002, 124, 9008
30. M. Movassaghi, M. A. Schmidt, Angew. Chem. 2007, 119, 3799
31. Angew. Chem. Int. Ed. 2007, 46, 3725
32. J. Kim, J. A. Ashenhurst, M. Movassaghi, Science 2009, 324, 238
33. T. Newhouse, P. S. Baran, J. Am. Chem. Soc. 2008, 130, 10886
34. K. Foo, T. Newhouse, I. Mori, H. Takayama, P. S. Baran, Angew. Chem. 2011, 123, 2768
35. Angew. Chem. Int. Ed. 2011, 50, 2716
36. K. M. Depew, S. P. Marsden, D. Zatorska, A. Zatorski, W. G. Bornmann, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 11953.
37. M. C. Willis, J. Chem. Soc. Perkin Trans. 1 1999, 1765
38. M. C. Willis, L. H. W. Powell, C. K. Claverie, S. J. Watson, Angew. Chem. 2004, 116, 1269
39. Angew. Chem. Int. Ed. 2004, 43, 1249
40. S. J. Byrne, A. J. Fletcher, P. Hebeisen, M. C. Willis, Org. Biomol. Chem. 2010, 8, 758
41. R. H. Snell, R. L. Woodward, M. C. Willis, Angew. Chem. 2011, 123, 9282
42. Angew. Chem. Int. Ed. 2011, 50, 9116.
43. Á. Enríquez-García, E. P. Kündig, Chem. Soc. Rev. 2012, 41, 7803
44. C. E. Müller, P. R. Schreiner, Angew. Chem. 2011, 123, 6136
45. Angew. Chem. Int. Ed. 2011, 50, 6012
46. E. García-Urdiales, I. Alfonso, V. Gotor, Chem. Rev. 2011, 111, PR 110
47. M. D. Díaz de Villegas, J. A. Gálvez, P. Etayo, R. Badorrey, P. Lõpez-Ram-de-Víu, Chem. Soc. Rev. 2011, 40, 5564.
48. O. Kitagawa, K. Yosumoto, M. Kohriyama, Y. Dobashi, T. Taguchi, Org. Lett. 2004, 6, 3605
49. O. Kitagawa, S. Matsuo, K. Yosumoto, T. Taguchi, J. Org. Chem. 2006, 71, 2524
50. M. Anstiss, J. M. Holland, A. Nelson, J. R. Titchmarsh, Synlett 2003, 1213
51. M. Anstiss, A. Nelson, Org. Biomol. Chem. 2006, 4, 4135
52. K. Takenaka, N. Itoh, H. Sasai, Org. Lett. 2009, 11, 1483
53. L. Porosa, R. D. Viirre, Tetrahedron Lett. 2009, 50, 4170
54. R. S. Ward, Chem. Soc. Rev. 1990, 19, 1
55. F. O. Arp, G. C. Fu, J. Am. Chem. Soc. 2006, 128, 14264
56. K. Rossen, P. J. Pye, A. Maliakal, R. P. Volante, J. Org. Chem. 1997, 62, 6462.
57. B. M. Trost, A. Aponick, J. Am. Chem. Soc. 2006, 128, 3931
58. B. M. Trost, D. E. Patterson, Chem. Eur. J. 1999, 5, 3279
59. B. M. Trost, D. E. Patterson, J. Org. Chem. 1998, 63, 1339
60. G. Muchow, J. M. Brunel, M. Maffet, O. Pardigon, G. Buono, Tetrahedron 1998, 54, 10435
61. B. M. Trost, Z. Shi, J. Am. Chem. Soc. 1996, 118, 3037.
62. H. Ishikawa, H. Takayama, N. Aimi, Tetrahedron Lett. 2002, 43, 5637
63. H. Takayama, Y. Matsuda, K. Masubuchi, A. Ishida, M. Kitajima, N. Aimi, Tetrahedron 2004, 60, 893
64. Y. Matsuda, M. Kitajima, H. Takayama, Heterocycles 2005, 65, 1031.
65. A. Jarrahpour, M. Zarei, Synlett 2008, 381
66. P. Jacob, P. S. Callery, A. T. Shulgin, N. Castagnoli, J. Org. Chem. 1976, 41, 3627.
67. Q. Shen, J. F. Hartwig, Org. Lett. 2008, 10, 4109.
68. During our investigations a report by Hou and co-workers was published on the kinetic resolution of indolines by means of a Trost allylation:, X. L. Hou, B. J. Zheng, Org. Lett. 2009, 11, 1789
69. for a recent review of non-enzymatic kinetic resolution see:, H. Pellissier, Adv. Synth. Catal. 2011, 353, 1613.
70. Z. Lu, S. Ma, Angew. Chem. 2008, 120, 264
71. Angew. Chem. Int. Ed. 2008, 47, 258
72. B. M. Trost, V. L. Van Ranken, Chem. Rev. 1996, 96, 395
73. B. M. Trost, Pure. Appl. Chem. 1996, 68, 779.
74. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082
75. C. C. C. Johansson, T. J. Colacot, Angew. Chem. 2010, 122, 686
76. Angew. Chem. Int. Ed. 2010, 49, 676.
77. M. J. Durbin, M. C. Willis, Org. Lett. 2008, 10, 1413
78. R. A. Altman, A. M. Hyde, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 9613
79. A. M. Taylor, R. A. Altman, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 9900
80. C. Mai, M. F. Sammons, T. Sammakia, Org. Lett. 2010, 12, 2306.
81. Synthesised by a procedure based on that reported by, Y. Yamada, S. Arima, C. Okada, A. Akiba, Y. Kai, Y. Harigaya, Chem. Pharm. Bull. 2006, 54, 788.
82. V. Snieckus, Chem. Rev. 1990, 90, 879.
83. D. L. Hughes, U. H. Dolling, K. M. Ryan, E. F. Schoenewaldt, E. J. J. Grabowski, J. Org. Chem. 1987, 52, 4745
84. T. B. K. Lee, G. S. K. Wong, J. Org. Chem. 1991, 56, 872
85. B. M. Trost, M. U. Frederiksen, Angew. Chem. 2005, 117, 312
86. Angew. Chem. Int. Ed. 2005, 44, 308.
87. K. Szabõ-Pusztay, L. Szabõ, Synthesis 1979, 276.
88. J. R. Fuchs, R. L. Funk, Org. Lett. 2005, 7, 677.
89. S. Escoubet, S. Gastaldi, M. Bertand, Eur. J. Org. Chem. 2005, 3855
90. J. K. Stille, Y. Becker, J. Org. Chem. 1980, 45, 2139
91. B. Alcaide, P. Almendros, J. M. Alonso, M. F. Aly, Org. Lett. 2001, 3, 3781
92. F. Garro-Helion, A. Merzouk, F. Guibé, J. Org. Chem. 1993, 58, 6109
93. J. Hine, S. M. Linden, A. Wang, V. Thiagarajan, J. Org. Chem. 1980, 45, 2821.