Application of a catalytic palladium biaryl synthesis reaction, via C-H functionalization, to the total synthesis of Amaryllidaceae alkaloids

Tetrahedron

Volumn 60, Issue 44, 2004, Pages 9889-9900

  Torres, José C ^a   Pinto, Angelo C ^a   Garden, Simon J ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Amaryllidaceae alkaloids; Biaryl synthesis; C H activation; C H functionalization; Dehydrohalogenation; Indoledione; Palladium catalysis; Pyrrolophenanthridine

Indexed keywords

ALKALOID DERIVATIVE; ANHYDROLYCORIN 7 ONE; ANHYDROLYCORINE; ASSOANINE; BENZYL DERIVATIVE; BORANE DERIVATIVE; CARBON; DEHYDROANHYDROLYCORINE; DEHYDROASSOANINE; HALOGEN; HIPPADINE; N BENZYLISATIN; OXOASSOANINE; PALLADIUM; PRATOSINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; DEHALOGENATION; OXIDATION; PRECURSOR; PRIORITY JOURNAL; REDUCTION;

AMARYLLIDACEAE;

EID: 4644360018     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.08.030     Document Type: Article

References (88)

1. Hoshino, O. The Amaryllidaceae alkaloids. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 51; pp 323-424
2. (a) Tsuji, J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis; John Wiley and Sons. Inc.: New York, 1995.
3. (b) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: Oxford, 2000; Vol. 20.
4. M.A. Siddiqui, and V. Snieckus Tetrahedron Lett. 31 1990 1523 1526
5. M.G. Banwell, B.D. Bissett, S. Busato, C.J. Cowden, D.C.R. Hockless, J.W. Holman, R.W. Read, and A.W. Wu J. Chem. Soc., Chem. Commun. 1995 2551 2553
6. M. Iwao, H. Takehara, S. Obata, and M. Watanabe Heterocycles 38 1994 1717 1720
7. R. Grigg, A. Teasdale, and V. Sridharan Tetrahedron Lett. 32 1991 3859 3862
8. T. Itahara Synthesis 1979 151 152
9. D.S.C. Black, P.A. Keller, and N. Kumar Tetrahedron Lett. 30 1989 5807 5808
10. D.S.C. Black, P.A. Keller, and N. Kumar Tetrahedron 49 1993 151 164
11. R.F. Heck Org. React. 27 1982 345 390
12. A. de Meijere, and F.A. Meyer Angew. Chem., Int. Ed. Engl. 33 1994 2379 2411
13. W. Cabri, and I. Candiani Acc. Chem. Res. 28 1995 2 7
14. G.T. Crisp Chem. Soc. Rev. 27 1998 427 436
15. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009 3066
16. R. Grigg, V. Sridharan, P. Stevenson, S. Sukirthalingam, and T. Worakun Tetrahedron 46 1990 4003 4018
17. A.P. Kosikowski, and D. Ma Tetrahedron Lett. 32 1991 3317 3320
18. G.A. Kraus, and H. Kim Synth. Commun. 23 1993 55 64
19. E. Desarbre, and J.-Y. Mérour Heterocycles 41 1995 1987 1998
20. T. Harayama, A. Hori, H. Abe, and Y. Takeuchi Heterocycles 60 2003 2429 2434
21. T. Harayama, A. Hori, H. Abe, and Y. Takeuchi Tetrahedron 60 2004 1611 1616
22. H.J. Knölker, and S. Filali Synlett 2003 1752 1754
23. A.I. Meyers, and R.H. Hutchings Tetrahedron Lett. 34 1993 6185 6188
24. R.H. Hutchings, and A.I. Meyers J. Org. Chem. 61 1996 1004 1013
25. J.S. Parnes, D.S. Carter, L.J. Kurz, and L.A. Flippin J. Org. Chem. 59 1994 3497 3499
26. L.M. Stark, X.-F. Lin, and L.A. Flippin J. Org. Chem. 65 2000 3227 3230
27. D.C. Harrowven, D. Lai, and M.C. Lucas Synthesis 1999 1300 1302
28. W. Carruthers, and N. Evans J. Chem. Soc. Perkin Trans. 1 1974 1523 1525
29. T. Onaka, Y. Kanda, and M. Natsume Tetrahedron Lett. 1974 1179 1180
30. R.K.Y. Zee-Cheng, S.-J. Yan, and C.C. Cheng J. Med. Chem. 21 1978 199 203
31. U. Lauk, D. Duerst, and W. Fischer Tetrahedron Lett. 32 1991 65 68
32. A.M. Rosa, A.M. Lobo, P.S. Branco, S. Prabhakar, and M. Sa-da-Costa Tetrahedron 53 1997 299 306
33. O. Tsuge, T. Hatta, and H. Tsuchiyama Chem. Lett. 1998 155 156
34. A. Padwa, M. Dimitroff, A.G. Waterson, and T.H. Wu J. Org. Chem. 63 1998 3986 3997
35. K. Hayakawa, T. Yasukouchi, and K. Kanematsu Tetrahedron Lett. 28 1987 5895 5898
36. D.P. Meirás, E. Guitián, and L. Castedo Tetrahedron Lett. 31 1990 2331 2332
37. D. Pérez, E. Guitián, and L. Castedo Tetrahedron Lett. 33 1992 2407 2408
38. C. González, D. Pérez, E. Guitián, and L. Castedo J. Org. Chem. 60 1995 6318 6326
39. D. Pérez, G. Burés, E. Guitián, and L. Castedo J. Org. Chem. 61 1996 1650 1654
40. C. González, E. Guitián, and L. Castedo Tetrahedron Lett. 37 1996 405 406
41. A. Padwa, A.M. Brodney, B. Liu, K. Satake, and T. Wu J. Org. Chem. 64 1999 3595 3607
42. For reviews on methods for the synthesis of biaryl bonds consult: (a) S.P. Stanforth Tetrahedron 54 1998 263 303
43. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359 1469
44. F.D. Popp Adv. Heterocycl. Chem. 18 1975 1 59
45. J.F.M. Silva, S.J. Garden, and A.C. Pinto J. Braz. Chem. Soc. 12 2001 273 324 This article is freely available over the internet: http://jbcs.sbq.org.br/
46. A.C. Pinto, F.S.Q. Silva, and R.B. Silva Tetrahedron Lett. 35 1994 8923 8926
47. J.C. Torres, S.J. Garden, A.C. Pinto, N. Boechat, and F. da Silva Tetrahedron 55 1999 1881 1892
48. S.J. Garden, R.B. Silva, and A.C. Pinto Tetrahedron 58 2002 8399 8412
49. M. Julia, F. Le Goffic, J. Igolen, and M. Baillarge Tetrahedron Lett. 1969 1569 1571
50. B. Jiang, J.M. Smallheer, C. Amaral-Ly, and M.A. Wuonola J. Org. Chem. 59 1994 6823 6827
51. T.D. Cushing, J.F. Sanz-Cervera, and R.M. Williams J. Am. Chem. Soc. 118 1996 557 579
52. S.J. Garden, J.C. Torres, L.E. da Silva, and A.C. Pinto Synth. Commun. 28 1998 1679 1689
53. S.J. Garden, J.C. Torres, and A.C. Pinto J. Braz. Chem. Soc. 11 2000 441 446 This article is freely available over the internet: http://jbcs.sbq.org.br/
54. For other examples of palladium catalyzed reactions involving isatin substrates see: (a) F. Martinez, and H. Naarmann Synth. Met. 39 1990 195 203
55. V. Lisowski, M. Robba, and S. Rault J. Org. Chem. 65 2000 4193 4194
56. M. Oestreich, P.R. Dennison, J.J. Kodanko, and L.E. Overman Angew. Chem., Int. Ed. Engl. 40 2001 1439 1442
57. D. Ma, and Q. Wu Tetrahedron Lett. 42 2001 5279 5281
58. B.K. Albrecht, and R.M. Williams Tetrahedron Lett. 42 2001 2755 2757
59. J.C. Torres, R.A. Pilli, M.D. Vargas, F.A. Violante, S.J. Garden, and A.C. Pinto Tetrahedron 58 2002 4487 4492
60. T. Harayama, H. Toko, A. Hori, T. Miyagoe, T. Sato, H. Nishioka, H. Abe, and Y. Takeuchi Heterocycles 61 2003 513 520
61. A.M. Echavarren, B. Gómez-Lor, J.J. González, and O. de Frutos Synlett 2003 585 597
62. E.J. Hennesy, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 12084 12085
63. C. Amatore, and A. Jutand Acc. Chem. Res. 33 2000 314 321
64. H. Ossor, M. Pfeffer, J.T.B.H. Jastrzeski, and C.H. Stam Inorg. Chem. 26 1987 1169 1171
65. C.-S. Li, C.-H. Cheng, F.-L. Liao, and S.-L. Wang J. Chem. Soc., Chem. Commun. 1991 710 712
66. C.-S. Li, and D.-C. Jou Organometallics 12 1993 3945 3954
67. B. Sezen, and D. Sames J. Am. Chem. Soc. 125 2003 10580 10585 We have followed the example of these authors for the use of the terms C-H activation and C-H functionalisation
68. J. Cámpora, J.A. López, P. Palma, P. Valerga, E. Spillner, and E. Carmona Angew. Chem., Int. Ed. Engl. 38 1999 147 151
69. H.J. Knölker, and K.R. Reddy Chem. Rev. 102 2002 4303 4427 See Scheme 8 of page 4308
70. M. Catellani, and G.P. Chiusoli J. Organomet. Chem. 425 1992 151 154
71. B. Martín-Matute, C. Mateo, D.J. Cárdenas, and A.M. Echavarren Chem.-Eur. J. 7 2001 2341 2348
72. J.J. González, N. García, B. Gómez-Lor, and A.M. Echavarren J. Org. Chem. 62 1997 1286 1291
73. M. Brookhart, and M.L.H. Green J. Organomet. Chem. 250 1983 395 408
74. J. Cámpora, E. Gutiérrez-Puebla, J.A. López, A. Monge, P. Palma, D. Río, and E. Carmona Angew. Chem., Int. Ed. Engl. 40 2001 3641 3644
75. M. Catellani, C. Mealli, E. Motti, P. Paoli, E. Perez-Carreno, and P.S. Pregosin J. Am. Chem. Soc. 124 2002 4336 4346
76. J.H. Rigby, and M.E. Mateo Tetrahedron 52 1996 10569 10582 These authors prepared what they claimed to be 8b through a sequence of four reactions starting from a 4,5,6-trihydroindol-2-one derivative with a global yield of 9%
77. G.W. Gribble Chem. Soc. Rev. 1998 395 404
78. S. Ghosal, P.H. Rao, D.K. Jaiswal, Y. Kumar, and A.W. Frahm Phytochemistry 20 1981 2003 2007
79. S. Ghosal, K.S. Saini, and A.W. Frahm Phytochemistry 22 1983 2305 2309
80. T. Jeffery J. Chem. Soc. Chem. Commun. 1984 1287 1289
81. T. Jeffery Tetrahedron 52 1996 10113 10130
82. D.E. Ames, and A. Opalko Tetrahedron 40 1984 1919 1925
83. S.J. Garden, J.C. Torres, S.C.D. Melo, A.S. Lima, A.C. Pinto, and E.L.S. Lima Tetrahedron Lett. 42 2001 2089 2092
84. M.M. Abelman, L.E. Overman, and V.D. Tran J. Am. Chem. Soc. 112 1990 6959 6964
85. W.F. Barthel, and B.H. Alexander J. Org. Chem. 23 1958 1012 1014
86. S.A. Ahmad-Junan, and D.A. Whiting J. Chem. Soc., Perkin Trans. 1 1992 675 678
87. H. Tomioka, H. Kawasaki, N. Kobayashi, and K. Hirai J. Am. Chem. Soc. 117 1995 4483 4498
88. J. Homer, and M.C. Perry J. Chem. Soc. Chem. Commun. 1994 373 374