The nucleophilic addition/electrophilic ring closure route to bio-active heterocycles

Current Medicinal Chemistry

Volumn 3, Issue 2, 1996, Pages 139-152

  Perlmutter, Patrick ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BLASTMYCINONE; CALCIMYCIN; CIGUATOXIN; GLYCOSIDE; HETEROCYCLIC COMPOUND; MACROLIDE; PAMAMYCIN; UNCLASSIFIED DRUG;

DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 0029992829     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (52)

1. Sjöstrom, H.; Nilsson, R. Thalidomide and the Power of the Drug Companies Penguin: Harmondsworth, 1972.
2. Heathcock, C. H. In Asymmetric Synthesis, Morrison, J. D. Ed.; Academic Press: New York, 1984, Volume 3, Part B, Chapter 2.
3. For example, see Kobayashi, S.; Honbe, M.; Saito, Y. Tetrahedron 1994, 50, 9629-9642.
4. Eliel, E. L. In Asymmetric Synthesis, Morrison, J. D. Ed.; Academic Press: New York, 1983, Volume 2, Part A, Chapter 5.
5. (a) Harmange, J.-C.; Figadère, B. Tetrahedron Asymmetry 1993, 4, 1711-1754.
6. (b) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408.
7. (c) Boivin T. L. B. Tetrahedron 1987, 43, 3309-3362
8. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
9. Woodward, R. B. Angew. Chem. 1957, 69, 50-58.
10. Brockmann, H.; Henkel, W. Naturwissenschaften 1950, 37, 138-139.
11. Nakagawa, A.; Omura, S. In Macrolide Antibiotics, Omura, S. Ed.; Academic Press: Orlando, 1984, pp 37-84.
12. McCann, P. A.; Pogell, B. M. J. Antibiot. 1979, 32, 673-678.
13. Natsume, M.; Kondo, S.; Marumo, S. J. Chem. Soc., Chem. Commun. 1989, 1911-1913.
14. Kondo, S.; Yasui, K.; Natsume, M.; Katayama, M.; Marumo, S. J. Antibiot. 1988, 41, 1196-1204.
15. Natsume, M.; Yasui, K.; Kondo, S.; Marumo, S. Tetrahedron Lett. 1991, 32, 3087-3090.
16. Kondo, S.; Yasui, K.; Katayama, M.; Marumo, S.; Kondo, T.; Hattori, H. Tetrahedron Lett. 1987, 28, 5861-5864.
17. Evans, D. A. Aldrichimica Acta 1982, 15, 23-32.
18. Garavelas, A.; Mavropoulos, I.; Perlmutter, P.; Westman, G. Tetrahedron Lett. 1995, 36, 463-466.
19. Walkup, R. D.; Kim, S. W. J. Org. Chem. 1994, 59, 3433-3441.
20. For example, see Bartlett, P. A.; Meadows, J. D.; Ottow, E. J. Am. Chem. Soc., 1984, 106, 5304-5311.
21. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747-5750.
22. Li, W.; Nihira, T.; Sakuda, S.; Nishida, T.; Yamada, Y. J. Ferment Bioeng. 1992, 74, 214-217.
23. Yamada, Y.; Sugamura, K.; Kondo, K.; Yanagimoto, M.; Okada, H. J. Antibiot 1987, 40, 496-504.
24. Watanabe, K.; Tanaka, T.; Kukuhara, K.; Miyaira, N.; Yonehara, H.; Umezawa, H. J. Antibiot. Ser. A. 1957, 10, 39.
25. (a) Birch, A. J.; Cameron, D. W.; Harada, Y.; Rickards, R. W. J. Chem. Soc. 1961, 889-895.
26. (b) van Tamelen, E. E.; Dickie, J. P.; Loomans. M. E.; Dewey, R. S.; Strong, F. M. J. Am. Chem. Soc. 1961, 83, 1639-1646.
27. For example, see Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208.
28. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321-4324.
29. Bond, S.; Perlmutter, P. unpublished results.
30. Gillespie, N. C.; Lewis, R. J.; Pern, J. H.; Bourke, A. T. C.; Holmes, M. J.; Bourke, J. B.; Shields, W. J. Med. J. Aust. 1986, 145, 584-590.
31. Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386.
32. Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; MacLeod, J. K.; Shell, M. M. Toxicon 1991, 29, 1115-1127.
33. Lewis, R. J.; Sellin, M. Toxicon 1992, 30, 915-919.
34. Lewis, R. J.; Endean, R. Naunyn-Schmiedeberg's Arch. Pharmacol. 1986, 334, 313-322.
35. Benort, E.; Legrand, A. M.; Dubois, J. M. Toxicon 1986, 24, 357-364.
36. Lewis, R. J.; Wong Hoy, A. W. Toxicon 1993, 31, 437-446.
37. Holmes, M. J.; Lewis, R. J.; Poli, M. A.; Gillespie, N. C. Toxicon, 1991, 29, 761-775.
38. Lewis, R. J.; Norton, R. S.; Brereton, I.; Eccles, C. Toxicon 1993, 31, 637-643.
39. Sasaki, M.; Hasegawa, A.; Tachibana, K. Tetrahedron Lett. 1993, 34, 8489-8492.
40. Corey, E. J.; Jardine, D. P.; Virgil, S.; Yuen, P.-W.; Connel, R. D. J. Am. Chem. Soc. 1989, 111, 9243-9244.
41. Sasaki, M.; Masayuki, I.; Tachibana, K. J. Org. Chem. 1994, 59, 715-717.
42. Guy, S.; Perlmutter, P. unpublished results.
43. For a similar sequence involving a free radical ring closure, see Kraus, G. A.; Thurston, J. Tetrahedron Lett. 1987, 28, 4011-4044.
44. For a discussion and leading references, see Wang, X.; Gross, P. H. J. Org. Chem. 1995, 60, 1201-1206.
45. Boschetti, A.; Nicotra, F.; Panza, L.; Russo, G. J. Org. Chem. 1988, 53, 4181-4185.
46. Carcano, M.; Nicotra, F.; Panza, L.; Russo, G. J. Chem. Soc., Chem. Commun. 1989, 297-298.
47. Berger, J.; Rachlin, A. I.; Scott, W. E.; Sternbach, L. H.; Goldberg, M. W. J. Am. Chem. Soc. 1951, 73, 5295-5298.
48. Blount, J. F.; Westley, J. W. J. Chem. Soc., Chem. Commun. 1975, 533.
49. Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506-2526.
50. Bender, S. L., Ph. D. Thesis, Harvard University, 1986.
51. Prudhomme, M.; Dauphin, G.; Jeminet, G. J. Chem. Res. (S) 1987, 420.
52. Mavropoulos, I.; Perlmutter, P. Tetrahedron Lett. 1996, submitted.