The domino cycloaddition/N-acyliminium ion cyclization cascade

Abstract

Various applications of the domino cycloaddition/N-acyliminium ion cyclization cascade are reported. The key step in the process involves the generation of a reactive N-acyliminium ion by fragmentation of an amino substituted [4 + 2]-cycloadduct. The successful synthesis of a number of alkaloids by this sequence of reactions reveals the usefulness and importance of this unique domino cascade.

References

1. T.-L. Ho, Tandem Organic Reactions, Wiley-Interscience, New York, 1992; Frontiers in Organic Synthesis, Chem. Rev., 1996, 96, pp. 1–600; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131.
2. J. K. Sutherland, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 3, p. 341.
3. P. Canonne, R. Boulanger and M. Bernatchez, Tetrahedron Lett., 1987, 28, 4997; D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Flemming, Pergamon, Oxford, 1991, vol. 4, ch. 4.2; H. M. L. Davies, T. J. Clark and H. D. Smith, J. Org. Chem., 1991, 56, 3817; R. Grigg, P. Kennewell and A. J. Teasdale, Tetrahedron Lett., 1992, 33, 7789.
4. E. J. Corey and X. M. Cheng, The Logic of Chemical Synthesis, Wiley-Interscience: New York, 1989, p. 31.
5. S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137.
6. J. D. Winkler, Chem. Rev., 1996, 96, 167; W. R. Roush, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, New York, 1991, vol. 5, p. 513; 1,3-Dipolar ycloaddition Chemistry, ed. A. Padwa, Wiley-Interscience, New York, 1984, vols. I and II.
7. H. Hiemstra and W. N. Speckamp, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, pp. 1047–1082; W. N. Speckamp and H. Hiemstra, Tetrahedron, 1985, 41, 4367.
8. D. J. Hart, J. Org. Chem., 1981, 46, 367; D. J. Hart, J. Org. Chem., 1981, 46, 3576; D. J. Hart and K. Kanai, J. Org. Chem., 1982, 47, 1555; D. J. Hart and T. K. Yang, Tetrahedron Lett., 1982, 23, 2671; D. J. Hart and K. Kanai, J. Am. Chem. Soc., 1983, 105, 1255.
9. J. P. Marino, Jr., M. H. Osterhout, A. T. Price, M. A. Semones and A. Padwa, J. Org. Chem., 1994, 59, 5518.
10. A. Padwa and M. D. Weingarten, Chem. Rev., 1996, 96, 223; A. Padwa, J. P. Marino, Jr. and M. H. Osterhout, J. Org. Chem., 1995, 60, 2704; A. Padwa, D. L. Hertzog, W. R. Nadler, M. H. Osterhout and A. T. Price, J. Org. Chem., 1994, 59, 1418; D. L. Hertzog, D. J. Austin, W. R. Nadler and A. Padwa, Tetrahedron Lett., 1992, 33, 4731; M. H. Osterhout, W. R. Nadler and A. Padwa, Synthesis, 1994, 123.
11. M. Sato, N. Kanuma and T. Kato, Chem. Pharm. Bull., 1982, 30, 1315; M. Regitz, J. Hocker and A. Leidhergener, Org. Synth., 1973, Coll. Vol. V, 179.
12. A. Padwa, M. A. Brodney, J. P. Marino, Jr., M. H. Osterhout and A. T. Price, J. Org. Chem., 1997, 62, 67.
13. H. Böhme and K. Hartkke, Chem. Ber., 1963, 96, 600; H. Hiemstra, H. P. Fortgens, S. Stegenga and N. W. Speckamp, Tetrahedron Lett., 1985, 26, 3151.
14. S. M. Weinreb and J. I. Levin, Heterocycles, 1979, 12, 949; S. Jendrzejewski and W. Steglich, Chem. Ber., 1981, 114, 1337.
15. T. Shono, H. Hamaguchi and Y. Matsumura, J. Am. Chem. Soc., 1975, 97, 4264.
16. V. M. Csizmadia, K. M. Koshy, K. C. M. Lau, R. A. McClelland, V. J. Nowlan and T. T. Tidwell, J. Am. Chem. Soc., 1979, 101, 974; A. Brossi, L. A. Dolan and S. Teital, Org. Synth., 1977, 56, 3.
17. A. Padwa, M. A. Brodney, J. P. Marino, Jr. and S. M. Sheehan, J. Org. Chem., 1997, 62, 78.
18. G. Stork, R. A. Kretchmer and R. H. Schlessinger, J. Am. Chem. Soc., 1968, 90, 1647; G. Stork, Pure Appl. Chem., 1968, 17, 383.
19. C. H. Heathcock, E. Kleinman and E. S. Binkley, J. Am. Chem. Soc., 1978, 100, 8036.
20. A. Mondon, K. F. Hansen, K. Boehme, H. P. Faro, J. H. Nestler, H. G. Vilhuber and K. Böttcher, Chem. Ber., 1970, 103, 615; A. Mondon and P. R. Seidel, Chem. Ber., 1971, 104, 2937; A. Mondon and H. J. Nestler, Chem. Ber., 1979, 112, 1329.
21. M. D. Weingarten, M. Prein, A. T. Price, J. P. Snyder and A. Padwa, J. Org. Chem., 1997, 62, 2001.
22. A. Padwa and A. T. Price, J. Org. Chem., 1995, 60, 6258; A. Padwa and A. T. Price, J. Org. Chem., 1998, 63, 556.
23. A. Padwa, D. L. Hertzog and W. R. Nadler, J. Org. Chem., 1994, 59, 7072.
24. G. A. Cordell, in The Alkaloids, ed. R. H. F. Manske and R. G. A. Rodrigo, Academic Press, New York, 1979, vol. 17, pp. 199–384; J. E. Saxton, Nat. Prod. Rep., 1993, 10, 349; 1994, 11, 493.
25. For some examples of amino-substituted furan Diels–Alder reactions, see J. E. Cochran, T. Wu and A. Padwa, Tetrahedron Lett., 1996, 37, 2903; R. H. Schlessinger and C. P. Bergstrom, Tetrahedron Lett., 1996, 37, 2133; R. H. Schlessinger, X. H. Wu and T. R. R. Pettus, Synlett, 1995, 536; R. H. Schlessinger, T. R. R. Pettus, J. P. Springer and K. Hoogsteen, J. Org. Chem., 1994, 59, 3246; R. H. Schlessinger and C. P. Bergstrom, J. Org. Chem., 1995, 60, 16.
26. C. O. Kappe, S. S. Murphree and A. Padwa, Tetrahedron, 1997, 53, 14179; S. Woo and B. Keay, Synthesis, 1996, 669; F. M. Dean, Adv. Heterocycl. Chem., 1981, 30, 168.
27. P. Chiu and M. Lautens, Top. Curr. Chem., 1997, 190, 1.
28. A. Padwa, M. Dimitroff, A. G. Waterson and T. Wu, J. Org. Chem., 1997, 62, 4088.
29. M. P. Cava, C. L. Wilson and C. J. Williams, J. Am. Chem. Soc., 1956, 78, 2303.
30. D. D. Sternbach, D. M. Rossana and K. D. Onan, J. Org. Chem., 1984, 49, 3427; M. E. Jung and J. Gervey, J. Am. Chem. Soc., 1989, 111, 5469; L. L. Klein, J. Org. Chem., 1985, 50, 1770.
31. P. A. Grieco, Aldrichim. Acta, 1991, 24, 61; P. A. Grieco, J. J. Nunes and M. D. Gaul, J. Am. Chem. Soc., 1990, 112, 4595; H. Waldman, Angew. Chem., Int. Ed. Engl., 1991, 30, 1306.
32. J. M. Llabres, F. Viladomat, J. Bastida, C. Codina and M. Rubiralta, Phytochemistry, 1986, 25, 2637.
33. S. Ghosal, P. H. Rao, D. K. Jaiswal, Y. Kumar and A. W. Frahm, Phytochemistry, 1985, 24, 1825; D. Perez, G. Bures, E. Guitian and L. Castedo, J. Org. Chem., 1996, 61, 1650.
34. R. K. Hill, in The Alkaloids, ed. R. H. F. Manske, Academic Press, New York, 1967, vol. 9, p. 483.
35. R. H. Hutchings and A. I. Meyers, J. Org. Chem., 1996, 61, 1004 and references cited therein.
36. O. DeLucchi, U. Miotti and G. Modena, Organic Reactions, ed. L. A. Paquette, Wiley, 1991, ch. 3, pp. 157–184.
37. D. S. Grierson and H. P. Husson, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, Oxford, 1991, vol. 6, pp. 909–947.
38. M. Kennedy and M. A. McKervey, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, Oxford, 1991, vol. 7, pp. 193–216.
39. P. D. Magnus, T. Gallagher, P. Brown and J. C. Huffman, J. Am. Chem. Soc., 1984, 106, 2105; P. Magnus, M. Giles, R. Bonnert, G. Johnson, C. McQuire, M. Deluca, A. Merrit, C. S. Kim and N. Vicker, J. Am. Chem. Soc., 1993, 115, 8116.
40. A. Padwa, D. E. Gunn and M. H. Osterhout, Synthesis, 1997, 1353.
41. A. De Groot and B. J. M. Jansen, J. Org. Chem., 1984, 49, 2034; B. J. M. Jansen, C. T. Bouwman and A. De Groot, Tetrahedron Lett., 1994, 35, 2977.
42. J. E. Cochran and A. Padwa, Tetrahedron Lett., 1995, 36, 3495; J. E. Cochran and A. Padwa, J. Org. Chen., 1995, 60, 3938; A. Padwa, J. E. Cochran and C. O. Kappe, J. Org. Chem., 1996, 61, 3706.
43. W. Eberbach, H. Fritz and N. Laber, Angew. Chem., Int. Ed. Engl., 1988, 27, 568; A. Schönig, T. Debaerdemaeker, M. Zander and W. Friedrichsen, Chem. Ber., 1989, 122, 1119; L. Aβmann, L. Palm, M. Zander and W. Friedrichsen, Chem. Ber., 1991, 124, 2481; G. W. Gribble, D. J. Keavy, D. A. Davis, M. G. Saulnier, B. Pelcman, T. C. Barden, M. P. Sibi, E. R. Olson and J. BelBruno, J. Org. Chem., 1992, 57, 5878.
44. C. O. Kappe and A. Padwa, J. Org. Chem., 1996, 61, 6166.
45. A. Padwa, C. O. Kappe, J. E. Cochran and J. P. Snyder, J. Org. Chem., 1997, 62, 2786.
46. J. L. Ripoll and Y. Vallee, Synthesis, 1993, 659.
47. A. Padwa, C. O. Kappe and T. S. Reger, J. Org. Chem., 1996, 61, 4888; A. Padwa, R. Hennig, C. O. Kappe and T. S. Reger, J. Org. Chem., 1988, 63 in the press.
48. T. Mukaiyama, K. Kamio, S. Kobayashi and H. Takei, Bull. Chem. Soc. Jpn., 1972, 45, 3723.
49. Y. Tsuda, S. Hosoi, A. Nakai, Y. Sakai, T. Abe, Y. Ishi, F. Kiuchi and T. Sano, Chem. Pharm. Bull., 1991, 39, 1365.