Catalytic tin radical mediated tricyclisations. Part 1. Monocyclisation studies

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 10, 2000, Pages 1559-1569

  Kelly, David R ^a   Picton, Mark R ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; ALCOHOLS; ALKYLATION; AROMATIC COMPOUNDS; CATALYSIS; TIN;

TRICYCLIZATION;

FREE RADICAL REACTIONS;

EID: 0034697423     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b000661k     Document Type: Article

References (110)

1. W. P. Neumann, Synthesis, 1987, 665.
2. E. J. Corey and J. W. Suggs, J. Org. Chem., 1975,40, 2554.
3. I. Terstiege and R. E. Maleczka, J. Org. Chem., 1999, 64, 342.
4. D. Crich and S. X. Sun, J. Org. Chem., 1996,61, 7200 and references therein. In our experience the best of these procedures is acetonitrile-hexane partition (J. M. Berge and S. M. Roberts, Synthesis, 1979, 471), although the product must be fairly polar, otherwise extraction into the acetonitrile phase is inefficient.
5. D. P. Curran, S. Hadida, S. Y. Kimand Z. Y. Luo, J. Am. Chem. Soc., 1999, 121, 6607;
6. J. H. Horner, F. N. Martinez, M. Newcomb, S. Hadida and D. P. Curran, Tetrahedron Lett., 1997, 38, 2783.
7. R. Rai and D. B. Collum, Tetrahedron Lett., 1994, 35, 6221;
8. D. L. J. Clive and W. Yang, J. Org. Chem., 1995, 60, 2607;
9. E. Vedejs, S. M. Duncan and A. R. Haight, J. Org. Chem., 1993, 58, 3046.
10. For reviews of applications in natural product synthesis see M. Ramaiah, Tetrahedron, 1987, 43, 3541;
11. G. P. Jasperse, D. P. Curran and T. L. Fevig, Chem. Rev., 1991, 91, 1237;
12. B. Giese, B. Kopping, T. Gobel, J. Dickhaut, G. Thoma, K. J. Kulicke and F. Trach, Org. Re act., 1996, 48, 301.
13. For a rare exception see, D. P. Curran and A. E. Gabarda, Tetrahedron, 1999, 55, 3327.
14. J. E. Baldwin, D. R. Kelly and C. B. Ziegler, J. Chem. Soc., Chem. Commun., 1984, 133;
15. D. R. Kelly and J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1985, 682.
16. For a discussion of radical reactions in retrosynthetic planning see, D. P. Curran, Synlett, 1991, 63.
17. Reviews: M. Malacria, Chem. Rev., 1996, 96, 289;
18. R. Gigg (ed.), Tetrahedron, symposium-in-Print No. 35, 1996, 52, 11385-11664;
19. A. Martinez-Graz and J. Marco-Contelles, Chem. Soc. Rev., 1998, 27, 155;
20. G. Pattenden and S. Handa, Contemp. Org. Synth., 1997, 4, 196;
21. F. Aldabbaah and W. R. Bowman, Contemp. Org. Synth., 1997, 4, 261.
22. For radical induced polycyclisations see S. Handa and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 1999, 843;
23. K. Takasu, J. Kuroyanagi, A. Katsumata and M. Ihara, Tetrahedron Lett., 1999, 40, 6277;
24. M. Breithor, U. Herden and H. M. R. Hoffmann, Tetrahedron, 1997, 53, 8401;
25. S. Bogen, L. Fensterbank and M. Malacria, J. Org. Chem., 1999, 64, 819;
26. U. Jahn and D..P. Curran, Tetrahedron Lett., 1995, 36, 8921;
27. P. Devin, L. Fensterbank and M. Malacria, J. Org. Chem., 1998, 63, 6764;
28. W. R. Bowman, P. T. Stephenson and A. R. Young, Tetrahedron, 1996, 52, 11445
29. and other radical cascade reactions, E. Lee, C. U. Hur, Y. H. Rhee, Y. C. Park and S. Y. Kim, J. Chem. Soc., Chem. Commun., 1993, 1466.
30. First presented in a lecture at ChemSpec Europe 94, Manchester, 19-20th April, 1994; D. R. Kelly, BACS Symp. Proc., 1994, 101;
31. D. R. Kelly, Spec. Chem., 1995, 68;
32. D. R. Kelly, Agro Food Industry, Hi-tech, 1995, 6, 33.
33. C. Anies, L. Billot, J.-Y. Lallemand and A. Pancrazi, Tetrahedron Lett., 1995, 36, 7247.
34. C. Spino and N. Barriault, J. Org. Chem., 1999, 64, 5292.
35. J. Marco-Contelles, Chem. Commun., 1996, 2629. Structure 2 in this paper is an incorrect regioisomer (corrigendum 1997, 725). Structure 5 should be the 4-O-propenyl derivative rather than the propynyl derivative. This was not corrected in the corrigendum;
36. A. Martinez-Graz and J. Marco-Contelles, Chem. Soc. Rev., 1998, 27, 155.
37. For related palladium catalysed bicyclisation reactions see, C. W. Holzapfel and L. Marais, Tetrahedron Lett., 1997, 38, 8585;
38. J.-F. Nguefack, V. Bolitt and D. Sinou, Tetrahedron Lett., 1996, 37, 59;
39. J.-F. Nguefack, V. Bolitt and D. Sinou, J. Org. Chem., 1997, 62, 6827.
40. R. J. Ferrier, J. Chem Soc., 1964, 5443-5449;
41. R. J. Ferrier, N. Prasad and G. H. Sankey, J. Chem Soc. (C), 1968, 974;
42. R. J. Ferrier and N. Prasad, J. Chem Soc. (C), 1969, 570.
43. B. Fraser-Reid, Acc. Chem. Res., 1975, 8, 192;
44. B. Fraser-Reid, Acc. Chem. Res., 1985, 18, 347;
45. B. Fraser-Reid and R. C. Anderson, Prog. Chem. Org. Nat. Prod., 1980, 39, 1;
46. N. L. Holder, Chem. Rev., 1982, 82, 287.
47. S. Hanessian, Total Synthesis of Natural Products: The 'Chiron' Approach, Pergamon Press, Oxford, 1983.
48. E. Maudru, G. Singh and R.' H. Wightman, Chem. Commun., 1998, 1505;
49. R. McCague, R. G. Pritchard, R. J. Stoodley and D. S. Williamson, Chem. Commun., 1998, 2691.
50. K. Toshima, T. Ishizuka, G. Matsua, M. Nakata and M. Kinoshita, J. Chem. Soc., Chem. Commun., 1993, 704.
51. B. S. Babu and K. K. Balasubramanian, Synlett, 1999, 1261;
52. B. S. Babu and K. K. Balasubramanian, Tetrahedron Lett., 1999, 40, 5777.
53. T. Linker, T. Sommermann, T. Gimisis and C. Chatgilialoglu, Tetrahedron Lett., 1998, 39, 9637.
54. F. W. Lichtenthaler and B. Werner, Carbohydr. Res., 1999, 319, 47;
55. B. K. Banik, O. Zegrocka, M. Manhas and A. K. Bose, Heterocycles, 1997, 46, 173;
56. M. Koreeda, T. A. Houston, B. K. Shull, E. Klenke and R. J. Tuinman, Synlett, 1995, 90.
57. J. C. Lopez, A. M. Gomez, S. Valerde and B. Fraser-Reid, J. Org. Chem., 1995, 60, 3851;
58. J. C. Lopez and B. Fraser-Reid, J. Chem. Soc., Chem. Commun., 1992, 94.
59. B. Fraser-Reid and S. Jarousz, unpublished method.
60. M. J. Robins, S. D. Hawrelak, T. Kanai, J. Siefert and R. Mengel, J. Org. Chem., 1979, 44, 1317.
61. M. P. Georgiadis and E. A. Couladouros, J. Heterocycl. Chem., 1991, 28, 1325.
62. 1H FT N MR Spectra, Aldrich Chemical Company, Milwaukee, 1993, furfuryl alcohol, vol. 3, 18A.
63. F. M. Hauser, S. R. Ellenberger and W. P. Ellenberger, Tetrahedron Lett., 1988, 29, 4939 and references therein.
64. G. Lauer and F. Oberdorfer, Angew. Chem., Int. Ed. Engl, 1993, 32, 272.
65. J. Marco-Contelles and M. Gema, Syntlt. Commun., 1997, 27, 725.
66. B. Fraser-Reid, A. McLean and E. W. Ushenvood, J. Am. Chem. Soc., 1969, 91, 5392.
67. S. K. Chaudhary and O. Hernandez, Tetrahedron Lett., 1979, 99.
68. E. J. Corey and A. Ventateswarlu, J. Am. Chem. Soc., 1972, 94, 6190.
69. H. S. Rhinesmith, J. Org. Chem., 1975, 40, 1773.
70. W. J. Balfour, C. G. Grieg and S. Visaisouk, J. Org. Chem., 1974, 40, 725;
71. M. E. Jung and K. R. Buszek, J. Am. Chem Soc., 1988, 110, 3965.
72. B. Neises and W. Steglich, Angew. Chem., Int. Ed. Engl, 1978, 17, 522.
73. E. Haslam, Tetrahedron, 1980,36, 2409.
74. L. Balas, B. Jousseaume and B. Langwost, Tetrahedron Lett., 1989, 30, 4525.
75. G. Stork and R. Mook, Jnr., J. Am. Chem. Soc., 1987, 109, 2829.
76. S. Satoh, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 1991, 56, 2278.
77. E. Lee, S.-B. Go and K. W. Jung, Tetrahedron Lett., 1989, 30, 827.
78. E. Lee, C.-U. Hur and J.-H. Park, Tetrahedron Lett., 1989, 30, 7219.
79. E. Lee, C. H. Yoon, T. H. Lee, S. Y. Kim, T. J. Ha, Y-S. Sung, S.-H. Park and S. Lee, J. Am. Chem. Soc., 1998, 120, 7469;
80. cf. C. Andres, J. P. Duque-Soladana and R. Pedrosa, Chem. Commun., 1999, 31.
81. Y Chapleur and N. Mound, J. Chem. Soc., Chem. Commun., 1989, 39;
82. N. Moufid and Y Chapleur, Tetrahedron Lett., 1991, 32, 1799;
83. N. Moufid, Y Chapleur and P. Mayon, J. Chem. Soc., Perkin Trans. I, 1992, 991;
84. N. Moufid, Y Chapleur and P. Mayon, J. Chem. Soc., Perkin Trans. 1, 1992, 999; Structure 14 in the last paper is the 1-O-(prop-2′-ynyl) derivative, whereas the correct structure is the 1-O-(but-3′-ynyl)-derivative.
85. J. E. Brumwell, N. S. Simpkins and N. K. Terrett, Tetrahedron, 1994, 50, 13533.
86. R. J. Ferrier, P. M. Petersen and M. A. Taylor, J. Chem. Soc., Chem. Commun., 1989, 1247;
87. R. J. Ferrier and P. M. Petersen, Tetrahedron, 1990, 46, 1.
88. G. E. Keck and J. B. Yates, J. Organomet. Chem., 1983, 248, C21.
89. W. E. Lindesell, P. N. Preston and A. B. Rettie, Carbohydr. Res., 1994, 254, 311.
90. P. W. Collins, C. A. Jung, A. Gasiecki and R. Pappo, Tetrahedon Lett., 1978, 3187;
91. M. E. Jung and L. A. Light, Tetrahedron Lett., 1982, 23, 3851;
92. S.-M. L. Chen, R. E. Schaub and G. V. Grudzinskas, J. Am. Chem. Soc., 1978, 43, 3450.
93. For 6-(π-exo)-endo-trig cyclisations, A. M. Gomez, G. O. Danelon, S. Valverde and J. Christobal Lopez, J. Org. Chem., 1998, 63, 9626; erratum,
94. A. M. Gomez, G. O. Danelon, S. Valverde and J. Christobal Lopez, J. Org. Chem., 1999, 64, 7280.
95. C. Lesueur, R. Nouguier, M. P. Bertrand, P. Hoffmann and A. De Mesmaeker, Tetrahedron, 1994, 50, 5369;
96. A. De Mesmaeker, P. Hoffmann and B. Ernst, Tetrahedron Lett., 1989, 30, 57;
97. A. De Mesmaeker, P. Hoffmann, B. Ernst, P. Hug and T. Winkler, Tetrahedron Lett., 1989, 30, 6307.
98. A. J. Fatiadi, Synthesis, 1976, 65;
99. J. S. Pizey, Synthetic Reagents, vol. 2, pp. 143-174, Halstead Press, New York, 1974.
100. B. Fraser-Reid, A. McLean and E. W. Usherwood, J. Am. Chem. Soc., 1969, 91, 5392;
101. B. Fraser-Reid, A. McLean, E. W. Ushenvood and M. Yunker, Can. J. Chem., 1970, 48, 2877.
102. HiMass, D. R. Kelly, unpublished work, 1991.
103. Multiplet, release NMRUC51, D. R. Kelly, unpublished work, 1995.
104. RACCOON, P. F. Schatz, University of Wisconsin, 1988.
105. PC-Model, Version 3.2, Sierra Software, Bloomington, IN, 1989.
106. 3)-H; C. A. G. Haasnoot, F. A. A. M. De Leeuw and C. Altona, Tetrahedron, 1981, 36, 2783;
107. cf. C. Altona, R. Francke, R. De Haan, J. H. Ippel, G. J. Daalmans, A. J. A. W. Hoekzema and J. van Wijk, Magn. Reson. Chem., 1994, 32, 670;
108. 2)-H; E. W. Garbish, J. Am. Chem. Soc., 1964, 86, 5561.
109. E. Pretsch, W. Simon, J. Seibl and T. Clerc, Tables of Spectral Data for Structure Determination of Organic Compounds, Springer-Verlag, Berlin, 1989, p. H215.
110. Implemented in the computer program Shoolery's Rules, S. D. Bull, unpublished work, 1989.