Synthetic studies in the intramolecular carbocyclization of N-acyloxyiminium ions. Stereoelectronic and steric implications of nucleophilic alkene, alkyne, and allene tethers

Journal of Organic Chemistry

Volumn 70, Issue 13, 2005, Pages 5070-5085

  Hanessian, Stephen ^a   Tremblay, Martin ^a   Marzi, Mauro ^a,b   Del Valle, Juan R ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b Sigma Tau SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; OLEFINS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AZACYCLIC COMPOUNDS; CARBOCYCLIZATION; LEWIS ACIDS; TRICYCLIC COMPOUNDS;

ORGANIC COMPOUNDS;

4 (3 BUTENYL); 4 (3 BUTYNYL); 4 (3 CINNAMYLMETHYL); 4 ALLENIC TETHER; 6 HALO HEXAHYDROINDOLE 2 CARBOXYLIC ACID; 6 HALO OCTAHYDROINDOLE 2 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; LEWIS ACID; PYROGLUTAMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 20844431887     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050326w     Document Type: Article

References (140)

1. (a) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431.
2. (b) Royer, J.; Bonin, M.; Micouin, J. Chem. Rev. 2004, 104, 2311.
3. Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
4. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: New York, 1991; Vol. 2, p 1047.
5. (e) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
6. (f) Speckamp, W. N. Recl. Trau. Chim. Pays-Bas 1981, 100, 345.
7. For selected reviews, see: (a) Micheal, J. P. Nat. Prod. Rep. 2003, 20, 458.
8. (b) Micheal, J. P. Nat. Prod. Rep. 2002, 19, 719.
9. Stribuya, S.; Yokomatsu, T.; Yuasa, Y. In Studies in Natural Products Chemistry; Attu-ur-Rahman, Ed., Elsevier: New York, 1993; Vol. 12, p 445.
10. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: London, UK, 1991; Vol. 2, p 1007.
11. (e) Ikeda, M.; Sato, T.; Ishibashi, H. Heterocycles 1988, 27, 1467.
12. (f) Hart, D. J. Alkaloids: Chem. Biol. Perspect. 1988, 6, 227.
13. For selected examples of cyclization in formic acid, see: (a) Brosius, A. D.; Overman, L. E. J. Org. Chem. 1997, 62, 440.
14. (b) Hart, D. J.; Hong, W. P. J. Org. Chem. 1985, 50, 3670.
15. Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316.
16. Wijnberg, B. P.; Speckamp, W. N. Tetrahedron Lett. 1980, 21, 1991.
17. (e) Schoemaker, H. E.; Dijkink, J.; Speckamp, W. N. Tetrahedron 1978, 34, 163. For cyclization with Lewis acid, see:
18. (f) Frank, K. E.; Aube, J. Tetrahedron Lett. 1998, 39, 7239.
19. (g) Rutjes, F. P. J. T.; Hiemstra, H.; Pirrung, F. O. H.; Speckamp, W. N. Tetrahedron 1993, 49, 10027.
20. (h) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. J. Chem. Soc., Perkin Trans. 2 1992, 857.
21. Esch, P. M.; Boska, I. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1991, 47, 4039.
22. (j) Moeller, K. D.; Ruthfus, S. L.; Wong, P. L. Tetrahedron 1991, 49, 583.
23. (k) Chu, W.; Moeller, K. D. Tetrahedron Lett. 1999, 40, 7939.
24. Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106.
25. Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155.
26. (n) Belleau, B. Can. J. Chem. 1957, 35, 651. For related cyclizations on N- and C-tethered iminium ions, see:
27. (o) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907.
28. (p) Heathcock, C. H.; Hansen, M. M.; Ruggeri, R. B.; Kath, J. C J. Org. Chem. 1992, 57, 2544.
29. (q) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 36, 3102.
30. Speckamp, W. N. In Stereoselective Synthesis of Natural Products; Workshop Conference Hoechst; Bartmann, W., Winterfeldt, E., Eds.; Elsevier: Amsterdam, The Netherlands, 1979; Vol. 7, pp 50-61; see also ref 1a.
31. (a) Ito, T.; Yamazaki, N.; Kibayashi, C. Synlett 2001, 10, 1506.
32. (b) Ollero, L.; Mentink, G.; Rutjes, F. P. J. T.; Speckamp, W. N.; Hiemstra, H. Org. Lett. 1999, 1, 1331.
33. Van der Vliet, P. N. W.; Hamersma, J. A. M.; Speckamp, W. N. Tetrahedron 1985, 41, 2007.
34. Hart, D. J.; Kanal, K.-I. J. Am. Chem. Soc. 1983, 105, 1255.
35. (e) Hamersma, J. A. M.; Speckamp, W. N. Tetrahedron 1982, 38, 3255.
36. (f) Wijnberg, B. P.; Speckamp, W. N.; Oostveen, A. R. C. Tetrahedron 1982, 38, 209.
37. (g) Wijnberg, J. B. P.; Speckamp, W. N. Tetrahedron Lett. 1981, 22, 5079.
38. (h) Nossin, P. M. M.; Speckamp, W. N. Tetrahedron Lett. 1980, 21, 1991.
39. Schoemaker, H. E.; Boer-Terpstra, Tj.; Dijkink, J.; Speckamp, W. N. Tetrahedron 1980, 36, 143.
40. (j) Dijkink, J.; Speckamp, W. N. Heterocycles 1979, 12, 1147.
41. (k) Dijkink, J.; Speckamp, W. N. Tetrahedron 1978, 34, 173.
42. For examples involving solvolysis with formic acid, see: (a) Kano, S.; Yokomatsu, T.; Nemoto, H.; Shibuya, S. Tetrahedron Lett. 1985, 26, 1531.
43. (b) Schoemaker, H. E.; Kruk, C.; Speckamp, W. N. Tetrahedron Lett. 1979, 2437.
44. Evans, D. A.; Thomas, E. W. Tetrahedron Lett. 1979, 411.
45. Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515.
46. (e) Oostveen, A. R. C.; de Boer, J. J. J.; Speckamp, W. N. Heterocycles 1977, 7, 171. See also ref 5b. For Lewis acids and alkene tethers, see:
47. (f) Luker, T.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220.
48. (g) Shono, T.; Matsumura, Y.; Uchida, K.; Tagami, K. Chem. Lett. 1987, 919.
49. (h) Melching, K. H.; Hiemstra, H.; Klaver, W. J.; Speckamp, W. N. Tetrahedron Lett. 1986, 27. 4799.
50. Shono, T.; Matsumura, Y.; Uchida, K; Kobayashi, H. J. Org. Chem. 1985, 50, 3243. For solvolysis of allenic or acetylenic tethers, see:
51. (j) Beyersbergen van Henegouwen, W. G.; Fieseler, R. M.; Rutjes, F. P. J. T.; Hiemstra, H. J. Org. Chem. 2002, 65, 8317.
52. (k) Beyersbergen van Henegouwen, W. G.; Hiemstra, H. J. Org. Chem. 1997, 62, 8862. For related addition of C-tethered enol on N-acyloxyiminium ions, see:
53. Wijnberg, J. B. P.; Speckamp, W. N. Tetrahedron 1978, 34, 2579.
54. Wijnberg, J. B. P.; Speckamp, W. N. Tetrahedron Lett. 1975, 3963. For applications to β-lactams, see:
55. (n) Metais, E.; Overman, L. E.; Rodriguez, M. I.; Stearns, B. A. J. Org. Chem. 1997, 62, 9210.
56. Hanessian, S.; Tremblay, M.; Petersen, J. W. J. Am. Chem. Soc. 2004, 126, 6064.
57. For a review, see: (a) Blechert, S. Synthesis 1989, 71. For examples, see:
58. (b) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687.
59. Hart, D. J.; Yang, T. K. J. Org. Chem. 1985, 50, 235.
60. Overman, L. E.; Jacobsen, E. J.; Doedens, R. J. J. Org. Chem. 1983, 48, 3393.
61. (e) Overman, L. E.; Kakimoto, M. A. J. Am. Chem. Soc. 1979, 101, 1310.
62. Hanessian, S.; Tremblay, M. Org. Lett. 2004, 6, 4683.
63. (a) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515.
64. (b) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; Chapter 6. For Prins cyclization, see:
65. Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079.
66. An analogy with the Stork-Eschenmoser proposals for polyene cyclizations has been made, see: (a) Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014.
67. (b) Stork, G.; Bugstahler, A. W. J. Am. Chem. Soc. 1955, 77, 5068.
68. Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890.
69. (a) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054.
70. (b) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 2833.
71. Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454.
72. Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
73. (e) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645.
74. (f) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146.
75. (a) Overman, L. E.; Lesuisse, D.; Hashimoto, M. J. Am. Chem. Soc. 1983, 105, 5373. For a review, see:
76. 1,3 strain in N-acyloxyiminium ions, see:
77. Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445.
78. Beak, P.; Zajdel, W. J. J. Am. Chem. Soc. 1984, 106, 1010.
79. (e) Hart, D. J. J. Am. Chem. Soc. 1980, 102, 397.
80. (f) Quick, J.; Mondello, C.; Humora, M.; Brennan, T. J. Org. Chem. 1978, 43, 2705.
81. (g) Fraser, R. R.; Grindley, T. B. Tetrahedron Lett. 1974, 416.
82. (h) Chow, Y. L.; Colon, C. J.; Tam, J. N. S. Can. J. Chem. 1968, 46, 2821.
83. Scott, J. W.; Durham, L. J.; Dejongh, H. A. P.; Burkhardt, V.; Johnson, W. S. Tetrahedron Lett. 1967, 2381. For a review, see:
84. (j) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
85. For the isolation, see: (a) Carroll, A. R.; Pierens, G.; Fechner, G.; de Almeidaleona, P.; Ngo, A.; Simpson, M.; Hooper, J. N. A.; Bostrom, S. L.; Musil, D.; Quinn, R. J. J. Am. Chem. Soc. 2002, 124, 13340. For the total synthesis, see:
86. (b) Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L. J. Am. Chem. Soc. 2002, 124, 13342.
87. (a) Müller, T.; Juhasz, M.; Reed, C. A. Angew. Chem., Int. Ed. 2004, 43, 1543.
88. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337.
89. McGibbon, G. A.; Brook, M. A.; Terlouw, J. K. J. Chem. Soc., Chem. Commun. 1992, 360. For an example of different reactivity between substituted and terminal alkynes, see:
90. Moeller, K. D.; Rothfus, S. L.; Wong, P. L. Tetrahedron 1991, 47, 583.
91. (e) Lambert, J. B. Tetrahedron 1990, 46, 2677.
92. (f) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496.
93. (g) Apeloig, Y.; Stanger, A. J. Org. Chem. 1982, 47, 1462.
94. (h) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549.
95. Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386.
96. (j) Hanack, M. Acc. Chem. Res. 1976, 9, 364.
97. (k) Schleyer, P. v. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513.
98. Hanack, M. Acc. Chem. Res. 1970, 3, 209.
99. Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521.
100. (n) Miller, L. L.; Kaufman, D. A. J. Am. Chem. Soc. 1968, 90, 7282.
101. Pardron, J. M.; Kobotos, G.; Martin, T.; Markidis, T.; Gibbons, W. A.; Martin, V. S. Tetrahedron: Asymmetry 1998, 9, 3381.
102. For the preparation of protected pyroglutamate derivatives, see: (a) Baldwin, J. E.; Miranda, T.; Moloney, M.; Hokelek, T. Tetrahedron 1989, 45, 7459.
103. (b) Jain, R. Org. Prep. Proc. Int. 2001, 33, 405.
104. Hanessian, S.; Margarita, R. Tetrahedron Lett. 1998, 39, 5887.
105. (a) Li, D.; Zhou, H.-Q.; Dakoji, S.; Shin, I.; Oh, E.; Liu, H.-W. I J. Am. Chem. Soc. 1998, 120, 2008.
106. (b) Crabbé, P.; Fillion, H.; André, D.; Luche, J.-L. J. Chem. Soc., Chem. Commun. 1979, 859.
107. (a) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4213.
108. ( b) Wipf, P.; Maresko, D. A. Tetrahedron Lett. 2000, 41, 4723.
109. Wipf, P.; Li, W. J. Org. Chem. 1999, 64, 4576.
110. Wipf, P.; Kim, Y.; Goustein, D. M. J. Am. Chem. Soc. 1995, 117, 1106.
111. (a) Valls, N.; López-Canet, M.; Vallribera, M.; Bonjoch, J. Chem. Eur. J. 2001, 7, 3446.
112. (b) Vails, N.; Lopez-Canet, M.; Vallribera, M.; Bonjoch, J. J. Am. Chem. Soc. 2000, 122, 11248.
113. Bonjoch, J.; Catena, J.; Isabal, E.; Lopez-Canet, M.; Valls, N. Tetrahedron: Asymmetry 1996, 7, 1899.
114. Bonjoch, J.; Catena, J.; Valls, N. J. Org. Chem. 1996, 61, 7106.
115. Ohshima, T.; Gnanadesikan, V.; Shibughushi, T.; Fukuta, Y.; Nemoto, T.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 11206.
116. (a) Toyooka, N.; Okumura, M.; Himiyama, T.; Nakazawa, A.; Nemoto, H. Synlett 2003, 55.
117. (b) Belvisi, L.; Colombo, L.; DiGiacomo, M.; Manzoni, L.; Vodopivec, B.; Scolastico, C. Tetrahedron 2001, 57, 6463.
118. (a) Rios Steiner, J. L.; Murakami, M.; Tulinsky, A. J. Am. Chem. Soc. 1998, 120, 597.
119. (b) Matsuda, H.; Okino, T.; Murakami, M.; Yamaguchi, K. Tetrahedron 1996, 52, 14501.
120. Murakami, M.; Ishida, K.; Okino, T.; Okita, Y.; Matsuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 2785.
121. Murakami, M.; Okita, Y.; Matsuda, H.; Okino, H.; Yamaguchi, K.; Tetrahedron Lett. 1994, 35, 3129. See also:
122. (e) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4213.
123. For example, see: Chamberlin, A. R.; Nguyen, D. H.; Chung, J. Y. L. J. Org. Chem. 1984, 49, 1682.
124. Wolfling, J.; Frank, E.; Schneider, G.; Bes, M. T.; Tietze, L. F. Synlett 1998, 1205.
125. (a) Suga, S.; Nagaki, A.; Tsutsui, Y.; Yoshida, J.-I. Org. Lett. 2003, 5, 945.
126. (b) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501.
127. Brocherieux-Lanoy, S.; Dhimane, H.; Poupon, J.-C.; Vanucci, C.; Lhommet, G. J. Chem. Soc., Perkin Trans. 1 1997, 2163.
128. Philli, R. A.; Dias, L. C.; Maldaner, A. O. J. Org. Chem. 1995, 60, 717.
129. (e) Esch, P. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1992, 48, 3445.
130. (f) Schmidt, R. R.; Hoffmann, A. R. Chem. Ber. 1974, 107, 78.
131. For a review, see: (g) Weinreb, S. M.; Scola, P. M. Chem. Rev. 1989, 89, 1525.
132. (h) Zaugg, H. E. Synthesis 1984, 85, 181.
133. Fisher, M. J.; Overman, L. E. J. Org. Chem. 1990, 55, 1447,
134. For an early example involving N-acyliminium ions, see: (a) Dijkink, J.; Schoemaker, H. E.; Speckamp W. N. Tetrahedron Lett. 1975, 16, 4043.
135. See also: (b) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687.
136. For examples of intramolecular silicon directed JV-acyliminium ion cyclizations, see ref 1a-f.
137. Heaney, H.; Taha, M. O. Tetrahedron Lett. 1998, 39, 3341.
138. For examples of allenes as π-nucleophiles, see: Nossin, P. M. M.; Speckamp, W. N. Tetrahedron Lett. 1981, 22, 3289. See also refs 6j,k.
139. (a) Ohkawa, T.; Imamura, K; Kurosaki, T.; Kobayashi, M.; Shimizu, S. PCT Int. Appl. 2004, WO2004111041; CAN 142, 56169.
140. (b) Barvian, N. C.; Connolly, C. J. C.; Guzzo, P. R.; Hamby, J. M.; Hicks, J. L.; Johnson, M. R.; Le, V.-D.; Mitchell, L. H.; Roark, W. H. PCT Int. Appl. 2004, WO 2004092132; CAN 141, 380130.