Construction of spiro[pyrrolidine-3,3′-oxindoles] - Recent applications to the synthesis of oxindole alkaloids

European Journal of Organic Chemistry

Volumn , Issue 12, 2003, Pages 2209-2219

  Marti, Christiane ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Alkaloids; Natural products; Spiro compounds; Total synthesis

Indexed keywords

ALKALOID DERIVATIVE; ALSTONISINE; COERULESCINE; ELACOMINE; HORSFILINE; OXINDOLE; PTEROPODINE; PYRROLIDINE DERIVATIVE; SALACIN; SPIRO COMPOUND; SPIRO(PYRROLIDINE 3,3' OXINDOLE) DERIVATIVE; SPIROTRYPROSTATIN A; SPIROTRYPROSTATIN B; STRYCHNOFOLINE; UNCLASSIFIED DRUG;

CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; SHORT SURVEY;

EID: 0038392407     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300050     Document Type: Short Survey

References (124)

1. J. S. Bindra, in: The Alkaloids (Ed.: R. H. F. Manske), Academic Press, New York, 1973, vol. 14, pp. 84-121.
2. A. Jossang, P. Jossang, H. A. Hadi, T. Sevenet, B. Bodo, J. Org. Chem. 1991, 56, 6527-6530.
3. C. B. Cui, H. Kakeya, H. Osada, J. Antibiot. 1996, 49, 832-835.
4. C. Pellegrini, M. Weber, H. J. Borschberg, Helv. Chim. Acta 1996, 79, 151-168.
5. R. T. Brown, in: Heterocyclic Compounds (Ed.: J. E. Saxon), Wiley Interscience, New York, 1983, vol. 25, part 4, pp. 85-97.
6. E. Wenkert, J. H. Udelhofen, N. K. Bhattacharyya, J. Am. Chem. Soc. 1959, 81, 3763-3768.
7. J. C. Seaton, M. D. Nair, O. E. Edwards, L. Marion, Can. J. Chem. 1960, 38, 1035-1042.
8. E. E. van Tamelen, J. P. Yardley, M. Miyano, W. B. Hinshaw, Jr., J Am. Chem. Soc. 1969, 91, 7333-7338.
9. Y. Ban, T. Oishi, Chem. Pharm. Bull. 1963, 11, 451-460.
10. E. Winterfeldt, A. J. Gaskell, T. Korth, H. E. Radunz, M. Walkowiak, Chem. Ber. 1969, 102, 3558-3572.
11. [11a] Y. Ban, T. Oishi, M. Seto, Tetrahedron Lett. 1972, 2113-2116.
12. [11b] Y. Ban, M. Seto, T. Oishi, Chem. Pharm. Bull. 1975, 23, 2605-2613.
13. D. Cartier, D. Patigny, J. Levy, Tetrahedron Lett. 1982, 23, 1897-1900.
14. [13a] K. Freter, H. Weissbach, B. Redfield, S. Udenfriend, B. Witkop, J. Am. Chem. Soc. 1958, 80, 983-987.
15. [13b] J. Harley-Mason, R. F. J. Ingleby, J. Chem. Soc. 1958, 3639-3642.
16. [13c] A. B. A. Jansen, C. G. Richards, Tetrahedron 1965, 21, 1327-1331.
17. [13d] R. T. Brown, R. Platt, Tetrahedron Lett. 1976, 2721-2722.
18. [13e] M. Seto, T. Oishi, H. Mitsuhashi, Y. Ban, Chem. Pharm. Bull. 1976, 24, 1393-1397.
19. [13f] E. Ali, P. K. Chakraborty, S. C. Pakrashi, Heterocycles 1982, 19, 1367-1370.
20. [13g] P. Rosenmund, M. Hosseini-Merescht, C. Bub, Liebigs Ann. Chem. 1994, 151-158.
21. [13h] M. Incze, G. Dornyei, M. Kajtar-Peredy, C. Szantay, Collect. Czech. Chem. Commun. 1999, 64, 408-416.
22. [13i] A. Patthy-Lukats, G. Beke, L. F. Szabo, B. Podanyi, J. Nat. Prod. 2001, 64, 1032-1039.
23. D. Ponglux, S. Wongseripipatana, N. Aimi, M. Nishimura, M. Ishikawa, H. Sada, J. Haginiwa, S. Sakai, Chem. Pharm. Bull. 1990, 38, 573-575.
24. S. I. Bascop, J. Sapi, J. Y. Laronze, J. Levy, Heterocycles 1994, 38, 725-732.
25. F. von Nussbaum, S. J. Danishefsky, Angew. Chem. Int. Ed. 2000, 39, 2175-2178.
26. A. Pictet, T. Spengler, Ber. Dtsch. Chem. Ges. 1911, 44, 2030.
27. A. Bischler, B. Napiralsky, Ber. Dtsch. Chem. Ges. 1893, 26, 1903-1908.
28. [19a] N. Finch, W. I. Taylor, J. Am. Chem. Soc. 1962, 84, 1318-1320.
29. [19b] N. Finch, W. I. Taylor, J. Am. Chem. Soc. 1962, 84, 3871-3877.
30. For a detailed discussion of the mechanism, see: [20al D. V. C. Awang, A. Vincent, D. Kindack, Can. J. Chem. 1984, 62, 2667-2675. [20b] R. Stahl, H. J. Borschberg, P. Acklin, Helv. Chim. Acta 1996, 79, 1361-1378.
31. For a detailed discussion of the mechanism, see: [20al D. V. C. Awang, A. Vincent, D. Kindack, Can. J. Chem. 1984, 62, 2667-2675. [20b] R. Stahl, H. J. Borschberg, P. Acklin, Helv. Chim. Acta 1996, 79, 1361-1378.
32. J. Shavel, H. Zinnes, J. Am. Chem. Soc. 1962, 84, 1320-1321.
33. [22a] S. F. Martin, M. Mortimore, Tetrahedron Lett. 1990, 31, 4557-4560.
34. [22b] S. F. Martin, B.; Benage, L. S. Geraci, J. E. Hunter, M. Mortimore, J. Am. Chem. Soc. 1991, 113, 6161-6171.
35. H. Takayama, N. Seki, M. Kitajima, N. Aimi, H. Seki, S. Sakai, Heterocycles 1992, 33, 121-125.
36. P. Yu, J. M. Cook, Tetrahedron Lett. 1997, 38, 8799-8802.
37. C. Pellegrini, C. Strässler, M. Weber, H. J. Borschberg, Tetrahedron: Asymmetry 1994, 5, 1979-1992.
38. S. D. Edmondson, S. J. Danishefsky, Angew. Chem. Int. Ed. 1998, 37, 1138-1140.
39. S. D. Edmondson, S. J. Danishefsky, L. Sepp-Lorenzino, N. Rosen, J. Am. Chem. Soc. 1999, 121, 2147-2155.
40. H. S. Wang, A. Ganesan, J. Org. Chem. 2000, 65, 4685-4693.
41. M. Somei, K. Noguchi, R. Yamagami, Y. Kawada, K. Yamada, F. Yamada, Heterocycles 2000, 53, 7-10.
42. N. Finch, I. H. C. Hsu, C. W. Gemenden, W. I. Taylor, J. Am. Chem. Soc. 1963, 85, 1520-1523.
43. H. Takayama, K. Masubuchi, M. Kitajima, N. Aimi, S. Sakai, Tetrahedron 1989, 45, 1327-1336.
44. A. C. Peterson, J. M. Cook, Tetrahedron Lett. 1994, 35, 2651-2654.
45. A. C. Peterson, J. M. Cook, J. Org. Chem. 1995, 60, 120-129.
46. [34a] p. Yu, J. M. Cook, J. Org. Chem. 1998, 63, 9160-9161.
47. [34b] p. Yu, T. Wang, J. Li, J. M. Cook, J. Org. Chem. 2000, 65, 3173-3191.
48. X. Z. Wearing, J. M. Cook, Org. Lett. 2002, 4, 4237-4240.
49. R. Grigg, M. F. Aly, V. Sridharan, S. Thianpatanagul, J. Chem. Soc. Chem. Commun. 1984, 182-183.
50. [37a] R. Grigg, V. Sridharan, S. Thianpatanagul, J. Chem. Soc., Perkin Trans. 1 1986, 1669-1675.
51. [37b] R. Grigg, S. Thianpatanagul, J. Kemp, Tetrahedron 1988, 44, 7283-7292.]
52. [37c] G. A. Kraus, J. O. Nagy, Tetrahedron 1985, 41, 3537-3545.
53. [37d] R. Grigg, G. Donegan, H. Q. N. Gunaratne, D. A. Kennedy, J. F. Malone, V. Sridharan, S. Thianpatanagul, Tetrahedron 1989, 45, 1723-1746.
54. [37e] A. Casaschi, G. Desimoni, G. Faita, A. G. Invernizzi, P. Grunanger, Gazz. Chim. Ital. 1993, 123, 137-143.
55. [37f] A. Casaschi, G. Desimoni, G. Faita, A. G. Invernizzi, P. Grunanger, Heterocycles 1994, 37, 1673-1686.
56. [37g] M. Nyerges, L. Gajdics, A. Söllõsy, L. Tõke, Synlett 1999, 111-113.
57. [37h] S. E. V. Bell, R. F. C. Brown, F. W. Eastwood, J. M. Horvath, Aust. J. Chem. 2000, 53, 183-190.
58. [37i] I. Fejes, M. Nyerges, A. Söllõy, G. Blaskó L. Tóke, Tetrahedron 2001, 57, 1129-1137.
59. [37j] R. Grigg, E. L. Millington, M. Thornton-Pett, Tetrahedron Lett. 2002, 43, 2605-2608.
60. G. Palmisano, R. Annunziata, G. Papeo, M. Sisti, Tetrahedron: Asymmetry 1996, 7, 1-4.
61. G. Cravotto, G. B. Giovenzani, T. Pilati, M. Sisti, G. Palmisano, J. Org. Chem. 2001, 66, 8447-8453.
62. N. Selvakumar, A. M. Azhagan, D. Srinivas, G. G. Krishna, Tetrahedron Lett. 2002, 43, 9175-9178.
63. P. R. Sebahar, R. M. Williams, J. Am. Chem. Soc. 2000, 122, 5666-5667.
64. P. R. Sebahar, H. Osada, T. Usui, R. M. Williams, Tetrahedron 2002, 58, 6311-6322.
65. K. Jones, J. Wilkinson, J. Chem. Soc., Chem. Commun. 1992, 1767-1769.
66. S. T. Hilton, T. C. T. Ho, G. Pljevaljcic, K. Jones, Org. Lett. 2000, 2, 2639-2641.
67. J. Cossy, M. Cases, D. G. Pardo, Tetrahedron Lett. 1998, 39, 2331-2332.
68. [46a] C. Escolano, K. Jones, Tetrahedron Lett. 2000, 41, 8951-8955.
69. [46b] C. Escolano, K. Jones, Tetrahedron 2002, 58, 1453-1464.
70. D. Lizos, R. Tripoli, J. A. Murphy, Chem. Commun. 2001, 2732-2733.
71. [48a] M. M. Abelman, T. Oh, L. E. Overman, J. Org. Chem. 1987, 52, 4130-4133.
72. [48b] A. Ashimori, L. E. Overman, J. Org. Chem. 1992, 57, 4571-4572.
73. [48c] A. Ashimori, B. Bachand, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6477-6487.
74. [48d] A. Ashimori, B. Bachand, M. A. Calter, S. P. Govek, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6488-6499.
75. [49a] W. G. Earley, T. Oh, L. E. Overman, Tetrahedron Lett. 1988, 29, 3785-3788.
76. [49b] A. Madin, C. J. O'Donnell, T. Oh, D. W. Old, L. E. Overman, M. J. Sharp, Angew. Chem. Int. Ed. 1999, 38, 2934-2936.
77. [49c] W. G. B. Beyersbergen van Henegouwen, R. M. Fieseler, F. Rutjes, H. Hiemstra, Angew. Chem. Int. Ecl. 1999, 38, 2214-2217.
78. [49d] W. G. B. Beyersbergen van Henegouwen, R. M. Fieseler, F. Rutjes, H. Hiemstra, J. Org. Chem. 2000, 65, 8317-8325.
79. L. E. Overman, M. D. Rosen, Angew. Chem. Int. Ed. 2000, 39, 4596-4599.
80. [51a] K. Fuji, M. Node, H. Nagasawa, Y. Naniwa, S. Terada, J. Am. Chem. Soc. 1986, 108, 3855-3856.
81. [51b] K. Fuji, M. Node, H. Nagasawa, Y. Naniwa, T. Taga, K. Machida, G. Snatzke, J. Am. Chem. Soc. 1989, 111, 7921-7925.
82. [52a] M. Node, H. Nagasawa, K. Fuji, J. Am. Chem. Soc. 1987, 109, 7901-7903.
83. [52b] M. Node, H. Nagasawa, K. Fuji, J. Org. Chem. 1990, 55, 517-521.
84. [52c] K. Fuji, T. Kawabata, T. Ohmori, M. Node, Synlett 1995, 367-368.
85. G. Lakshmaiah, T. Kawabata, M. H. Shang, K. Fuji, J. Org. Chem. 1999, 64, 1699-1704.
86. T. D. Bagul, G. Lakshmaiah, T. Kawabata, K. Fuji, Org. Lett. 2002, 4, 249-251.
87. U. K. S. Kumar, H. Ila, H. Junjappa, Org. Lett. 2001, 3, 4193-4196.
88. W. A. Bone, W. H. Perkin, J. Chem. Soc. 1895, 67, 108-119.
89. For a discussion on charge affinity patterns and retrosynthesis, see: D. A. Evans, G. C. Andrews, Acc. Chem. Res. 1974, 7, 147-155.
90. [58a] S. Danishefsky, J. Dynak, J. Org. Chem. 1974, 39, 1979-1980.
91. [58b] S. Danishefsky, J. Dynak, E. Hatch, M. Yamamoto, J. Am. Chem. Soc. 1974, 96, 1256-1259.
92. [58c] S. Danishefsky, S. J. Etheredge, J. Dynak, P. McCurry, J. Org. Chem. 1974, 39, 2658-2659.
93. [58d] S. Danishefsky, J. Dynak, Tetrahedron Lett. 1975, 79-80.
94. A. B. Smith III, R. M. Scarborough, Jr., Tetrahedron Lett. 1978, 19, 1649-1652.
95. L. Bagnell, A. Meisters, T. Mole, Aust. J. Chem. 1975, 28, 821-824.
96. [61a] R. D. Miller, D. R. McKean, J. Org. Chem. 1981, 46, 2412-2414.
97. [61b] R. K. Dieter, S. Pounds, J. Org. Chem. 1982, 47, 3174-3177.
98. 2 (L is a solvent molecule): E. J. Corey, W. D. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336.
99. 2, no reaction takes place. Additionally, N-benzyl-3(2-iodoethyl)oxindole was obtained as a byproduct in one of the ring expansion reactions. This compound is the keto form of enole 63 after aqueous workup.
100. The ring closure of iminium compound 64 to 60 is a disfavored 5-endo-trig cyclization process; see: [64a] J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734-736. [64b] J. E. Baldwin, R. C. Thomas, L. I. Kruse, L. Silberman, J. Org. Chem. 1977, 42, 3846-3852. [64c] D. D. Johnson, Acc. Chem. Res. 1996, 26, 476-482.
101. The ring closure of iminium compound 64 to 60 is a disfavored 5-endo-trig cyclization process; see: [64a] J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734-736. [64b] J. E. Baldwin, R. C. Thomas, L. I. Kruse, L. Silberman, J. Org. Chem. 1977, 42, 3846-3852. [64c] D. D. Johnson, Acc. Chem. Res. 1996, 26, 476-482.
102. The ring closure of iminium compound 64 to 60 is a disfavored 5-endo-trig cyclization process; see: [64a] J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734-736. [64b] J. E. Baldwin, R. C. Thomas, L. I. Kruse, L. Silberman, J. Org. Chem. 1977, 42, 3846-3852. [64c] D. D. Johnson, Acc. Chem. Res. 1996, 26, 476-482.
103. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
104. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
105. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
106. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
107. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
108. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
109. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
110. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
111. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
112. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
113. For other examples of 5-endo-trig cyclization processes, see; [65a] R. Grigg, J. Kemp, J. Malone, A. Tangthongkum, J. Chem. Soc. Chem. Commun. 1980, 648-650. [65b] p. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1985, 26, 4455-4458. [65c] A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807. [65d] A. D. Jones, D. W. Knight, Chem. Commun. 1996, 915-916. [65e] M. B. Berry, D. Craig, P. S. Jones, G. J. Rowlands, Chem. Commun. 1997, 2141-2142. [65e] D. Craig, P. S. Jones, G. J. Rowlands, Synlett 1997, 1423-1425. [65f] C. Dell'Erba, A. Mugnoli, M. Novi, M. Pani, G. Petrillo, C. Tavani, Eur. J. Org. Chem. 2000, 903-912. [65g] K. T. Chang, K. C. Jang, H. Y. Park, Y. K. Kim, K. H. Park, W. S. Lee, Heterocycles 2001, 55, 1173-1179. [65h] D. Craig, A. M. Smith, Tetrahedron Lett. 1992, 33, 695-698. [65i] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron Lett. 1995, 36, 7531-7534. [65j] D. Craig, N. J. Ikin, N. Mathews, A. M. Smith, Tetrahedron 1999, 55, 13471-13494.
114. The use of the 2-naphthylsulfonyl group as nitrogen protective group led to improved diastereoselectivity in some cases.
115. P. B. Alper, C. Meyers, A. Lerchner, D. R. Siegel, E. M. Carreira, Angew. Chem. Int. Ed. 1999, 38, 3186-3189.
116. [66] This discovery has been pursued by other research groups: [68a] M. Lautens, W. S. Han, J. Am. Chem. Soc. 2002, 124, 6312-6316. [68b] F. Bertozzi, M. Gustafsson, R. Olsson, Org. Lett. 2002, 4, 3147-3150. [68c] F. Bertozzi, M. Gustafsson, R. Olsson, Org. Lett. 2002, 4, 4333-4336.
117. [66] This discovery has been pursued by other research groups: [68a] M. Lautens, W. S. Han, J. Am. Chem. Soc. 2002, 124, 6312-6316. [68b] F. Bertozzi, M. Gustafsson, R. Olsson, Org. Lett. 2002, 4, 3147-3150. [68c] F. Bertozzi, M. Gustafsson, R. Olsson, Org. Lett. 2002, 4, 4333-4336.
118. [66] This discovery has been pursued by other research groups: [68a] M. Lautens, W. S. Han, J. Am. Chem. Soc. 2002, 124, 6312-6316. [68b] F. Bertozzi, M. Gustafsson, R. Olsson, Org. Lett. 2002, 4, 3147-3150. [68c] F. Bertozzi, M. Gustafsson, R. Olsson, Org. Lett. 2002, 4, 4333-4336.
119. The ring expansion of 62 with tosyl isocyanate and the transformations of pyrrolidinone 67 into compounds 68-72 were undertaken by A. Lerchner during his diploma studies: A. Lerchner, Diploma Thesis, ETH Zürich, 1999.
120. C. Fischer, C. Meyers, E. M. Carreira, Helv. Chim. Acta 2000, 83, 1175-1181.
121. L. Angenot, Plant. Med. Phytother. 1978, 12, 123.
122. A. Lerchner, E. M. Carreira, J. Am. Chem. Soc. 2002, 124, 14826-14827.
123. Only a single-intermediate purification was required.
124. C. Meyers, E. M. Carreira, Angew. Chem. Int. Ed. 2003, 42, 694-696.