Diels-Alder reactions in the synthesis of higher terpenes: Diels-Alder reactions in terpene synthesis

Organic Synthesis: Theory and Applications

Volumn 5, Issue C, 2001, Pages 39-87

  Brocksom, Timothy John ^a   Corrêa, Arlene G ^a   Naves, Ronilda M ^a   Silva, Fausto ^a   Catani, Valdomiro ^a   Ceschi, Marco A ^a   Zukerman Schpector, Julio ^a   Toloi, Ana Paula ^a   Ferreira, Maria Lúcia ^a   Brocksom, Ursula ^a  

^a FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84874818666     PISSN: 1047773X     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1047-773X(01)80003-2     Document Type: Article

References (103)

1. Ireland, r.E., Organic Synthesis. 1969, Prentice-Hall, Berlin.
2. Corey, e.J., Cheng, X.-M., The Logic of Chemical Synthesis. 1989, Wiley, Englewood Cliffs, NJ.
3. Warren, S., Organic Synthesis: the Disconnection Approach. 1982, Wiley, New York.
4. Anand, N., Bindra, j.S., Ranganathan, S., Art in Organic Synthesis. 1970, Holden-Day, Chichester.
5. Fleming, I., Selected Organic Syntheses. 1973, Wiley, San Francisco.
6. Bindra, j.S., Bindra, R., Creativity in Organic Synthesis. 1975, Academic, London.
7. Turner, S., The Design of Organic Syntheses. 1976.
8. Nicolaou, k.C., Sorensen, e.J., Classics in Total Synthesis. 1996, VCH, Elsevier, Amsterdam.
9. thematic issueFrontiers in Organic Synthesis. Vol. 2 Wender, p.A., (eds.) Chem. Rev., 96(1), 1996.
10. Organic Synthesis: Theory and Applications. Chapters 1 and 2 Hudlicky, T., (eds.), 1996, JAI, Weinheim.
11. Desimoni, G., Tacconi, G., Barco, A., Pollini, g.P., Natural Products Synthesis Through Pericyclic Reactions. ACS Monograph, 1983, 180.
12. Carruthers, W., Cycloaddition Reactions in Organic Synthesis. 1990, Pergamon, Greenwich, CT.
13. Fringuelli, F., Taticchi, A., Dienes in the Diels-Alder Reaction. 1990, Wiley, Oxford.
14. Trost, b.M., Fleming, I., Comprehensive Organic Synthesis. Paquette, l.A., (eds.), 1991, Pergamon, New York.
15. Advances in Cycloaddition. Curran, d.P., Lautens, M., (eds.) Advances in Cycloaddition, 1991, JAI, Oxford 4.
16. Corey, e.J., Ohno, M., Mitra, r.B., Vatakencherry, p.A., J.Am. Chem. Soc., 86, 1964, 478.
17. Corey, e.J., Mitra, r.B., Uda, H., J. Am. Chem. Soc., 86, 1964, 485.
18. Heathcock, c.H., The Total Synthesis of Natural Products., Chapter 4 ApSimon, J., (eds.) The Total Synthesis of Natural Products, 1973, Wiley, Greenwich, CT, 282–330 A.
19. Abad, A., Agulló, C., Arnó, M., Cantín, A., Cuñat, a.C., Meseguer, B., Zaragozá, r.J., J. Chem. Soc. Perkin Trans. 1, 1997, 1837.
20. Srikrishna, A., et al. J. Chem. Soc. Perkin Trans. 1, 1999, 2069 and references cited therein.
21. Ziegler, f.E., Hwang, K.-J., J. Org. Chem., 48, 1983, 3349.
22. Tenius, b.S. M., Rohde, a.R., Victor, m.M., Viegas, C Jr, Synth. Commun., 26, 1996, 197.
23. Ho, T.-L., Enantioselective Synthesis: Natural Products from Chiral Terpenes. 1992, Wiley, New York.
24. Ho, T.-L., Carbocycle Construction in Terpene Synthesis. 1988, VCH, New York.
25. Nerdel, F., Dahl, H., Liebigs Ann. Chem., 710, 1967, 90.
26. Harayama, T., Cho, H., Inubushi, Y., Tetrahedron Lett., 1975, 2693.
27. Chem. Pharm. Bull., 25, 1917, 2273.
28. Angell, e.C, Fringuelli, F., Pizzo, F., Porter, B., Taticchi, A., Wenkert, E., J. Org. Chem., 50, 1985, 4696.
29. Bohlmann, F., Forster, H.-J., Fischer, C.-H., Liebigs Ann. Chem., 1976, 1487.
30. Bohlmann, F., Eickeler, E., Chem. Ber., 113, 1980, 1189.
31. Yamakawa, K., Satoh, T., Chem. Pharm. Bull., 25, 1977, 2535.
32. Yamakawa, K., Satoh, T., Chem. Pharm. Bull., 26, 1978, 3704.
33. Dickinson, r.A., Kubela, R., MacAlpine, g.A., Stojanac, Z., Valenta, Z., Can. J. Chem., 50, 1972, 2377.
34. Stojanac, Z., Dickinson, r.A., Stojanac, N., Woznow, r.J., Valenta, Z., Can. J. Chem., 53, 1975, 616.
35. Stojanac, N., Sood, A., Stojanac, Z., Valenta, Z., Can. J. Chem., 53, 1975, 619.
36. Das, J., Kubela, R., MacAlpine, g.A, Stojanac, Z., Valenta, Z., Can. J. Chem., 57, 1979, 3308.
37. Tou, j.S., Reusch, W., J. Org. Chem., 45, 1980, 5012.
38. Kolaczkowski, L., Reusch, W., J. Org. Chem., 50, 1985, 4766.
39. Tegmo-Larsson, I.-M., Rozeboom, m.D., Houk, k.N., Tetrahedron Lett., 1981, 2043.
40. Rozeboom, m.D., Tegmo-Larsson, I.-M., Houk, k.N., J. Org. Chem., 46, 1981, 2338.
41. Hendrickson, j.B., Singh, V., J. Chem. Soc., Chem. Commun., 1983, 837.
42. Dauben, w.G., Farkas, L., Bridon, d.P., Chuang, C.-P., Henegar, k.E., J. Am. Chem. Soc., 113, 1991, 5883.
43. Arseniyadis, S., Rodriguez, R., Yashunsky, d.M., Camara, J., Ourisson, G., Tetrahedron Lett., 1994, 4843.
44. Fieser, l.F., Seligman, a.M., Ber. Dtsch. Chem. Ges., 68B, 1935, 1747.
45. Fieser, l.F., Seligman, a.M., J. Am. Chem. Soc., 56, 1934, 2690.
46. Sims, j.J., Honwad, v.K., Tetrahedron Lett., 1973, 2155.
47. Kienzle, F., Stadlweiser, J., Mergelsberg, I., Helv. Chim. Acta., 72, 1989, 348.
48. Aichberger, w.D., Aigner, J., Gossinger, E., Gruber, K., Menz, G., Monatsh. Chem., 1994, 991.
49. Aldrich catalog, 1998-1999, p. 1609, n° 27, 466-6; 5g. US$ 65.50. Legal importation of reagents into Brazil generally take at least one year!.
50. Aldrich catalog, 1998-1999, p. 1609, n° 11, 209-7; 500g US$ 46.90. A difference of 140 times! Furthermore thymol is readily available in Brazil for dent.
51. Dockal, e.R., Cass, q.B., Brocksom, t.J., Brocksom, U., Correa, a.G., Synth. Commun., 15, 1985, 1033.
52. Liotta, D., Arbiser, J., Short, W., Saindane, M., J. Org. Chem., 48, 1983, 2932.
53. Marchand, a.P., Allen, r.W., J. Org. Chem., 39, 1974, 1596.
54. Brocksom, t.J., Constantino, m.G., J. Org. Chem., 47, 1982, 3450.
55. Brocksom, t.J., Constantino, m.G., An. Acad. brasil Cienc., 54, 1982, 655.
56. Schmidt, C., J. Org. Chem., 35, 1970, 1324.
57. Liu, m.T. H., Schmidt, C., Tetrahedron, 27, 1971, 5289.
58. Schmidt, C., Can. J. Chem., 51, 1973, 3989.
59. Schmidt, C, Breining, T., Tetrahedron, 39, 1983, 3929.
60. Bold, G., Chao, S., Bhide, R., Wu, S.-H., Patel, d.V., Sih, c.J., Tetrahedron Lett., 1987, 1973.
61. White, J.D., Shin, H., Kim, T.-S., Cutshall, N.S., J.Am. Chem.Soc., 119, 1991, 2404.
62. Verkruijsse, h.D., de Graaf, W., Brandsma, L., Synth. Commun., 18, 1988, 131.
63. Iulek, J., Zukerman-Schpector, J., Brocksom, t.J., Silva, F. Jr., Acta Cryst., C49, 1993, 1657.
64. Iulek, J., Zukerman-Schpector, J., Brocksom, t.J., Silva, F. Jr., Acta Cryst., C50, 1994, 85.
65. Zukerman-Schpector, J., Caracelli, I., Silva, F. Jr, Brocksom, t.J., Acta Cryst., C52, 1996, 2354.
66. Caracelli, I., Iulek, J., Neves, A., Vencato, I., Silva, F. Jr, Brocksom, t.J., Acta Cryst., C53, 1997, 1282.
67. We thank Prof. Banwell for his important suggestions and experimental details on these nucleophilic addition reactionsBanwell, m.G., Hockless, d.C. R., Holman, j.W., Longmore, r.W., McRae, K.J., Pham, h.T. T., Synlett., 1999, 1491.
68. Zukerman-Schpector, J., Castellano, e.E., de Simone, c.A., Brocksom, t.J., Catani, V., Acta Cryst., C46, 1990, 1971.
69. Zukerman-Schpector, J., Castellano, e.E., Oliva, G., Brocksom, t.J., Catani, V., Acta Cryst., C47, 1991, 358.
70. Castellano, e.E., Brocksom, t.J., Ceschi, m.A., Acta Cryst., C50, 1994, 124.
71. Zukerman-Schpector, J., Castellano, e.E., Ceschi, m.A., Brocksom, t.J., Acta. Cryst., C53, 1997, 1482.
72. Trost, b.M., Haffner, c.D., Jebaratnam, d.J., Krische, m.J., Thomas, a.P., J. Am. Chem. Soc., 121, 1999, 6183.
73. Trost, b.M., Krische, m.J., J. Am. Chem. Soc., 121, 1999, 6131.
74. Sha, C.-K., Chiu, R.-T., Yang, C.-F., Yao, N.-T., Tseng, W.-H., Liao, F.-L., Wang, S.-L., J. Am. Chem. Soc., 119, 1997, 4130.
75. Oppolzer, W., Strauss, h.F., Simmons, d.P., Tetrahedron Lett., 23, 1982, 4673.
76. Collins, p.A., Wege, D., Aust. J. Chem., 32, 1979, 1819.
77. Antczak, K., Kingston, j.F., Fallis, a.G., Can. J. Chem., 63, 1985, 993.
78. Piers, E., Jung, g.L., Moss, N., Tetrahedron Lett., 25, 1984, 3959.
79. We thank Prof. Piers for reprints and many very stimulating discussions on sesquiterpene synthesisPiers, E., Jung, g.L., Can. J. Chem., 63, 1985, 996.
80. Hodgson, g.L., Mac Sweeney, d.F., Money, T., J. Chem. Soc. Perkin Trans. 1, 1973, 2113.
81. We thank Prof. Money for useful discussions on camphor chemistryEck, c.R., Hodgson, g.I., Macsweeney, d.F., Mills, r.W., Money, T., J. Chem. Soc. Perkin Trans., 1974, 1938.
82. Piers, E., Britton, r.W., Geraghty, m.B., Keziere, r.J., Smillie, r.D., Can. J. Chem., 53, 1975, 2827.
83. Piers, E., Britton, r.W., Geraghty, m.B., Keziere, r.J., Kido, F., Can. J. Chem., 53, 1975, 2838.
84. Liu, C., Burnell, d.J., J. Org. Chem., 62, 1997, 3683.
85. Liu, C., Burnell, d.J., Tetrahedron Lett., 38, 1997, 6573.
86. We thank Prof. Liotta for very helpful and explicative discussions, and also for experimental details on this particular pointLiotta, D., Saindane, M., Sunay, U., Jamison, w.C. L., Grossman, J., Phillips, P., J. Org. Chem., 50, 1985, 3241.
87. Tius, m.A., Chem. Rev., 88, 1988, 719.
88. Hanson, j.R., Nat. Prod. Rep., 16, 1999, 209.
89. Morita, H., Yoshida, N., Kobayashi, J., J. Org. Chem., 64, 1999, 7208.
90. Sugano, M., Shindo, T., Sato, A., Iijima, Y., Oshima, T., Kuwano, H., Hata, T., J. Org. Chem., 55, 1990, 5803.
91. Aigner, J., Gossinger, E., Kahlig, H., Menz, G., Pflugseder, K., Angew. Chem. Int. Ed., 37, 1998, 2226.
92. Toro, A., Wang, Y., Deslongchamps, P., Tetrahedron Lett., 40, 1999, 2765.
93. Ho, T.-L., Heterolytic Fragmentation of Organic Molecules, 1993, Wiley, Weinheim.
94. Weyerstahl, P., Marschall, H., Comprehensive Organic Synthesis. Trost, b.M., Fleming, I., Winterfeldt, E., (eds.), Chapter 5.4, 1991, Pergamon, New York.
95. Marshall, j.A., Synthesis, 1972, 517.
96. Trost, b.M., Fleming, I., Pattenden, G., Comprehensive Organic Synthesis, 3, 1991, Pergamon Chapter 3.
97. Yamamura, S., The Alkaloids, Academic, Vol. 29, 1991, Pergamon, 265 1986.
98. Orban, J., Turner, j.V., Tetrahedron Lett., 24, 1983, 2697.
99. Heathcock, c.H., Angew. Chem. Int., 31, 1992, 665.
100. earlier references cited. We thank Prof. Heathcock for helpful insights and information on this workHeathcock, c.H., Kath, j.C, Ruggeri, r.B., J. Org. Chem., 60, 1995, 1120.
101. Brocksom, t.J., Canevarolo, e.T., Lopes, f.T., An. Acad. bras. Ciênc., 57, 1985, 159.
102. Brocksom, t.J., Canevarolo, e.T., Lopes, f.T., An. Acad. bras. Ciênc., 57, 1985, 165.
103. Brocksom, t.J., Pesquero, e.T. C., Lopes, f.T., Synth. Commun., 20, 1990, 1181.