C-Acylnitrilium ion initiated cyclizations in heterocycle synthesis

Tetrahedron

Volumn 55, Issue 33, 1999, Pages 9947-9978

  Livinghouse, Tom ^a  

^a MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALKENE DERIVATIVE; DENDROBINE; IODIDE; ISONITRILE DERIVATIVE; ISOQUINOLINE DERIVATIVE; NITRILE; PYRROLINE DERIVATIVE; SAMARIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHINESE MEDICINE; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033551720     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00565-7     Document Type: Review

References (90)

1. For an abbreviated list of leading references, see: (a) Ruggeri, R. B.; McClure, K. F.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 11, 1530.
2. (b) Overman, L. E.; Robichaud, A. J. J. Am. Chem. Soc. 1989, 111, 300.
3. (c) Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658.
4. (d) Grieco, P.A.; Fobare, W. F. J. Chem. Soc., Chem. Commun. 1987, 185.
5. (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
6. (b) Williams, R. M.; Armstrong, R. W.; Dung, J. A. J. Am. Chem. Soc. 1985, 107, 3253.
7. For an elegant example of the use of nitrilium ions in total synthesis, see: Stevens, R. V.; Kenny, R. M. J. Chem. Soc., Chem. Commun. 1983, 384.
8. Westling, M.; Livinghouse, T. Tetrahedron Lett. 1985, 26, 5389.
9. Westling, M.; Smith, R.; Livinghouse, T. J. Org. Chem. 1986, 51, 1159.
10. Havlike, A.; Wald, M. M. J. Am. Chem. Soc. 1955, 77, 5171.
11. Nef, J. U. Justus Liebigs Ann. Chem. 1892, 270, 267.
12. 8b The reaction conditions employed in this early account were far harsher than necessary (benzene, reflux) and the product yields were presumably lowered as a consequence.
13. (b) Ugi, I.; Fetzer, U. Chem. Ber. 1961, 94, 1116.
14. The greater reactivity of acyl bromides permits the desired insertion reactions to be conducted at temperatures as low as 0 °C. In some instances this characteristic has proven advantageous.
15. An elegant synthesis of the erythrinane skeleton which utilizes a thionium ion cyclization has been published. Tamura, Y.; Maeda, H.; Akai, S.; Ishibashi, H. Tetrahedron Lett. 1982, 23, 2209.
16. Smith, R.; Livinghouse, T. J. Org. Chem. 1983, 48, 1554.
17. Smith, R.; Livinghouse, T. Tetrahedron 1985, 41, 3559.
18. The failure of certain nonstabilized azomethine ylides to undergo internal [3 + 2] cycloadditions with nonactivated dipolarophiles has also been noted by others: (a) Padwa, A.; Haffmans, G.; Thomas, M. J. Org. Chem. 1984, 49, 3314.
19. (b) Vedejs, E.; West, F. G. J. Org. Chem. 1983, 48, 4773.
20. The successful utilization of "stabilized" azomethine ylides in intramolecular [3 + 2] cycloadditions has been described: Confalone, P. N.; Huie, E. M. J. Am. Chem. Soc. 1984, 106, 7175 and references therein.
21. An alternative method for the pyrolytic generation of stabilized azomethine ylides has appeared. DeShong, P.; Kell, D. A.; Sidler, D. R. J. Org. Chem. 1985, 50, 2309.
22. Whaley, W. M.; Govindachari, T. R. In "Organic Reactions"; Adams, R. Ed., John Wiley: New York, 1951, Vol. 6, p 74.
23. The cyclization of 2-(2-furyl)ethyl amides has been accomplished in low to moderate yield through the use of modified Bischler-Napieralski reaction conditions. Herz, W.; Tocker, S. J. Am. Chem. Soc. 1955, 77, 3554.
24. The structure assigned to the erythrinane 10 was fully supported by proton decoupling experiments and nuclear Overhauser difference spectroscopy.
25. Westling, M.; Livinghouse, T. J. Am. Chem. Soc. 1987, 109, 590.
26. Luedtke, G.; Westling, M.; Livinghouse, T. Tetrahedron 1992, 48, 2209.
27. Schollkopf, U. Angew. Chem. Int. Ed. Engl. 1977, 16, 339.
28. Westling, M.; Livinghouse, T. Synthesis 1987, 391.
29. 1H NMR in the presence of pyridine.
30. 2Cl(1,2-DCE).
31. Evidence for the existence of a trans-fused B, C ring junction in 40 was provided by 300-MHz NOE experiments. A definitive assignment awaits single crystal X-ray structure determination.
32. Lee, C. H.; Westling, M.; Livinghouse, T.; Williams, A. C. J. Am. Chem. Soc. 1992, 114, 4089.
33. (a) Inubushi, Y.; Sasaki, Y.; Tsuda, Y.; Yasui, B.; Konka, T.; Matsumoto, J.; Katarao, E.; Nakano, J. Tetrahedron, 1964, 20, 2007.
34. (b) Inubushi, Y.; Sakaki, Y.; Tsuda, Y.; Nakano, J. Tetrahedron Lett. 1965, 1519.
35. (a) China's Pharmacopeia; Part I; The People's Health Sciences Publication Co.: Beijing, China, 1977; p 145.
36. (b) A Dictionary of Chinese Materia Medica; Jiangsu Medical College; Shanghai Scientific Technology Press: Shanghai, China, 1977; p 586.
37. (a) Chen, K. K.; Chen, A. L. J. Biol. Chem. 1935, 111, 653.
38. (b) Porter, L. Chem. Rev. 1967, 67, 441.
39. Akhita, M.; Botting, N. P.; Cohen, M. A.; Gani, D. Tetrahedron, 1987, 43, 5899.
40. 20
41. Fleet, G. H. W.; Harding, P. J. C. Tetrahedron Lett. 1979, 20, 975.
42. Brown, H. C.; Cha, J. S.; Nazer, B. Inorg. Chem. 1984, 23, 2929.
43. 34b was also examined as a reducing agent for the preparation of 42. In this instance 42 was produced along with its C-10 epimer in a ration of 93:7. In addition, the reaction was not amenable to scale up:
44. (b) Palmisano, G.; Lesma, G.; Nali, M. ; Rindone, B.; Tollari, S. Synthesis 1985, 1072.
45. Green, K. Tetrahedron Lett. 1989, 30, 4807.
46. Enholm, E. J.; Trivellas, A. J. Am. Chem. Soc. 1989, 111, 6463 and references therein.
47. Fevig, T. L.; Elliot, R. L.; Curran, D. P. J. Am. Chem. Soc. 1988, 110, 5064.
48. Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236 and references therein.
49. Beckwith, A. J. Tetrahedron 1981, 37, 3073.
50. (a) Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226.
51. (b) Luche, J. L.; Rodrigues, H. L.; Cragge, P. J. Chem. Soc., Chem. Commun. 1978, 601.
52. (a) Roush, W. R. J. Am. Chem. Soc. 1978, 100, 3599.
53. (b) Roush, W. R. J. Am. Chem. Soc. 1980, 102, 1390.
54. Luedtke, G.; Livinghouse, T. J. Chem. Soc., Perkin Trans. 1 1995, 2369.
55. (a) Ayer, W. A.; Kasitu, G. C. Can. J. Chem. 1989, 67, 1077;
56. (b) Yu, C.; Shen, W.; Han. J.; Chen Y.; Zhu, Y. Yaoxue Xuebao, 1982, 17, 795.
57. (a) Harayama, T.; Ohtani, M.; Oki, M.; Inubushi, Y. Chem Pharm. Bull., 1975, 23, 1511;
58. (b) Harayama, T.; Ohtani, M.; Oki, M.; Inubushi, Y. J. Chem. Soc., Chem. Commun. 1974, 827.
59. (a) Harayama, T.; Takatani, M.; Inubushi, Y. Chem. Pharm. Bull. 1980, 28, 2394;
60. (b) Harayama, T.; Takatani, M.; Inubushi, Y. Tetrahedron Lett. 1979, 20, 4307.
61. Inubushi, Y.; Ishii, H.; Harayama, T. Chem. Pharm. Bull. (Tokyo) 1967, 15, 250;
62. (b) Blumenkopf, T. A.; Heathcock, C. H. In The Alkaloids, S. W. Pelletier ed., John Wiley and Sons, New York, 1985, p 230.
63. Ishibashi, H.; So, T. S.; Sato, T., Kurado, K.; Ikeda, M. J. Chem. Soc., Chem. Commun. 1989, 762.
64. The tricyclic imines 67d and 67e were found to undergo slow decomposition at room temperature but could be stored indefinitely in a benzene matrix under argon at -20 °C.
65. Hughes, D. J.; Livinghouse, T. J. Chem. Soc., Perkin Trans. 1 1995, 2373.
66. Bick, I. R. C.; Hai, M. A. Heterocycles, 1981, 16, 1301.
67. 13C NMR and GC-mass spectral analysis.
68. The isonitrile 82 was prepared by the reaction of (2-chloroethylidene)cyclohexane with isocyanomethyllithium.
69. 4 (74% overall)] followed by N-formylation-dehydration.
70. (b) Baldwin, J. E.; Lusch, M. L. J. Org. Chem. 1979, 44, 1923.
71. Azabicyclo[3.3.1]nonane 86a was isolated from this mixture by careful chromatography on silica gel and was fully characterized.
72. The stereochemical disposition of the hydroxy group of 88 has not been determined.
73. Kercher, T.; Livinghouse, T. J. Org. Chem. 1997, 62, 805.
74. Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200.
75. For a comprehensive account dealing with the synthetic utility of allylsilanes and related compounds see: The Electrophilic Substitution of Allylsilanes and Vinylsilanes. Fleming, I.; Dunogues, J; Smithers, R. in Organic Reactions, Kende, A. S., Ed.; John Wiley and Sons; New York, 1989, Vol. 37, Chapter 2, p 57.
76. Several additional examples of stereocontrolled allylsilane-iminium ion cyclizations have appeared; (a) Heerding, D. A.; Hong, C. Y.; Kado, N.; Look, G. C.; Overman, L. E. J. Org. Chem. 1993, 58, 6947.
77. (b) Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028.
78. (c) Hiemstra, H.; Forgens, H. P.; Speckamp, W. N. Tetrahedron Lett. 1985, 26, 3155.
79. (d) Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014.
80. (a) Larsen, S. D.; Grieco, P. A.; Fobare, W. F. J. Am. Chem. Soc. 1986, 108, 3512;
81. (b) Grieco, P. A.; Fobare, W. F. Tetrahedron Lett. 1986, 27, 5067.
82. In contrast to allylsilanes, 2-propylidene-1,3-bis(silane)s have seen relatively little use in synthesis. For pertinent references concerning the use of these compounds as well as related methodology, see: (a) Rubiralt, M.; Diez, A.; Miguel, D. Syn. Commun. 1992, 22, 359.
83. (b) Guyot, B.; Pornet, J.; Miginiac, L. J. Organomet. Chem. 1990, 386, 19.
84. (c) Guyot, B.; Pornet, J.; Miginiac, L. Tetrahedron 1991, 47, 3981.
85. An account addressing stereoselective cyclizations of allylsilanes with nitrilium ions generated by a Beckmann rearrangement has appeared, see: Schinzer, D.; Bo, Y. Angew. Chem., Int. Ed. Engl. 1991, 30, 687.
86. Danishefsky, S.; McKee, R.; Singh, R. K. J. Am. Chem. Soc. 1977, 99, 771.
87. Krimen, L. I. in Organic Syntheses; Breslow, R., Ed.; John Wiley and Sons: New York, 1970; Vol. 50, p 1.
88. For a recent review, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
89. In contrast to the cis-pyrrolines, the only significant NOE enhancements that were observed upon irradiation of the C-4 and C-2 methine hydrogens in the minor trans isomers were to different hydrogens on the central C-3 methylene: (formula presented)
90. 4 (74% overall)] followed by N-formylation-dehydration.