Vinyl isocyanates as useful building blocks for alkaloid synthesis

Synlett

Volumn , Issue 1, 2000, Pages 1-12

  Rigby, James H ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

Cyclization; Cycloaddition; Hydroindolones; Isocyanates; Isocyanides; Pyridones

Indexed keywords

ALKALOID; BENZOPHENANTHRIDINE DERIVATIVE; INDOLE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; PHENANTHRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; PYRROLIDINE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 0033972360     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (60)

1. For an overview of pyridones, see: (a) Lednicer, D.; Mitscher, L. A. The Organic Chemistry of Drug Synthesis; Wiley: New York, all volumes.
2. (b) Grundon, M. F. In The Alkaloids, The Chemical Society: London, 1977; Vol. 7.
3. (c) Ninomiya, I.; Naito, Y. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1983; Vol. XXII, p 189.
4. (a) Dondoni, A.; Kniezo, L; Medici, A. J. Org. Chem. 1982, 47, 3994.
5. (b) Takaki, K.; Okamura, A.; Ohshiro, Y.; Agawa, T. J. Org. Chem. 1978, 43, 402.
6. (c) Fuks, R. Tetrahedron 1970, 26, 2161.
7. (d) Hart, R. Bull. Soc. Chim., Belg. 1956, 65, 291.
8. Enamine additions to aryl isocyanates had been recorded previously: Ried, W.; Kappeler, W. Liebigs Ann. Chem. 1965, 688, 177.
9. (a) Rigby, J. H.; Balasubramanian, N. J. Org. Chem. 1984, 49, 4569.
10. (b) For a different cycloaddition pathway of vinyl isocyanates, see: De Tollenaere, C.; Ghosez, L. Bull. Soc. Chim. Fr. 1997, 134, 989.
11. Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
12. Rigby, J. H.; Balasubramanian, N. J. Org. Chem. 1989, 54, 224.
13. Wall, M. E.; Wani, M. C. Cancer Res. 1995, 55, 753.
14. Rigby, J. H.; Danca, D. M. Tetrahedron Lett. 1997, 38, 4969.
15. Rigby, J. H.; Burkhardt, F. J. J. Org. Chem. 1986, 51, 1374.
16. Wat, C.-K.; McInnes, A. G.; Smith, D. G.; Wright, J. L. C.; Vining, L. C. Can. J. Chem. 1977, 55, 4090.
17. Rigby, J. H.; Qabar, M. J. Org. Chem. 1989, 54, 5852.
18. Rigby, J. H.; Wilson, J. Z. Tetrahedron Lett. 1984, 25, 1429.
19. Simanek, V. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 185-240.
20. (a) Hart, H.; Ok, D. J. Org. Chem. 1986, 51, 979.
21. (b) Campbell, C. D.; Rees, C. W. J. Chem. Soc. C 1969, 742.
22. Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem. 1989, 54, 4019.
23. Rigby, J. H.; Holsworth, D. D. Tetrahedron Lett. 1991, 32, 5757.
24. (a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127.
25. (b) Morel, G.; Marchand, E.; Foucaud, A.; Toupet, L. J. Org. Chem. 1990, 55, 1721.
26. (c) Westling, M.; Livinghouse, T. J. Am. Chem. Soc. 1987, 109, 590.
27. (d) Westling, M.; Smith, R.; Livinghouse, T. J. Org. Chem. 1986, 51, 1159.
28. Ugi, I.; Meyr, R.; Lipinski, M.; Bodesheim, F.; Rosendahl, F. Org. Synth.; Wiley: New York, 1973; Coll. Vol. 5; p 300.
29. Rigby, J. H.; Qabar, M. N. J. Am. Chem. Soc. 1991, 113, 8975.
30. Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569.
31. Rigby, J. H.; Qabar, M. N. J. Org. Chem. 1993, 58, 4473.
32. Beckwith, A. L. J.; Moad, G. J. Chem. Soc. Chem. Commun. 1974, 472.
33. (a) Overman, G. E. Pure Appl. Chem. 1994, 66, 1423.
34. (b) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, R. W. Tetrahedron 1993, 49, 5177.
35. Rigby, J. H.; Hughes, R. C.; Heeg, M. J. J. Am. Chem. Soc. 1995, 117, 7834.
36. Jeffery, T. Synthesis 1987, 70.
37. (a) Pole, D. L.; Sharma, P. K.; Warkentin, J. Can. J. Chem. 1996, 74, 1335.
38. (b) Arduengo, A. J., III; Dias, H. V. R.; Dixon, D. A.; Harlow, R. L.; Klooster, W. T.; Koetzle, T. F. J. Am. Chem. Soc. 1994, 116, 6812.
39. (c) Moss, R. A. Acc. Chem. Res. 1989, 22, 15.
40. Moss, R. A.; Wlostowski, M.; Shen, S.; Krogh-Jespersen, K.; Matro, A. J. Am. Chem. Soc. 1988, 110, 4443.
41. Hoffmann, R. W.; Steinbach, K.; Dittrich, B. Chem. Ber. 1973, 106, 2174.
42. (a) Couture, P.; Terlouw, J. K.; Warkentin, J. J. Am. Chem. Soc. 1996, 118, 4214.
43. (b) Kassam, K.; Pole, D. L.; El-Saidi, M.; Warkentin, J. J. Am. Chem. Soc. 1994, 116, 1161.
44. Rigby, J. H.; Cavezza, A.; Ahmed, G. J. Am. Chem. Soc. 1996, 118, 12848.
45. Rigby, J. H.; Cavezza, A.; Heeg, M. J. Tetrahedron Lett. 1999, 40, 2473.
46. Rigby, J. H.; Laurent, S. J. Org. Chem. 1999, 64, 1766.
47. Rigby, J. H.; Cavezza, A.; Heeg, M. J. J. Am. Chem. Soc. 1998, 120, 3664.
48. Rigby, J. H.; Laurent, S.; Cavezza, A.; Heeg, M. J. J. Org. Chem. 1998, 63, 5587.
49. For a review of some synthetic studies in this area, see: Polt, R. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, 1996; Vol. 3, p 104.
50. Ninomiya, I.; Naito, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1983, Vol. XXII, p 189.
51. Rigby, J. H.; Gupta, V. Synlett 1995, 547.
52. Pawlak, J. C.; Berchtold, G. A. J. Org. Chem. 1987, 52, 1765.
53. Burgess, E. M.; Penton, H. R, Jr.; Taylor, E. A. J. Org. Chem. 1973, 38, 26.
54. Williams, R. M.; Kwast, E. Tetrahedron Lett. 1989, 30, 451.
55. Rigby, J. H.; Mateo, M. F. J. Am. Chem. Soc. 1997, 119, 12655.
56. Rigby, J. H.; Laurent, S. J. Org. Chem. 1998, 63, 6742.
57. For an overview of Cr(0)-mediated cycloaddition, see: (a) Rigby, J. H. Acc. Chem. Res. 1993, 26, 579.
58. (b) Rigby, J. H. Tetrahedron 1999, in press.
59. Rigby, J. H.; Ahmed, G.; Ferguson, M. D. Tetrahedron Lett. 1993, 34, 5397.
60. Rigby, J. H.; Pigge, F. C. Synlett 1996, 631.