Studies directed towards the total synthesis of (+)-himbacine

Synthesis

Volumn , Issue SPEC. ISS. APR., 1998, Pages 479-489

  Hofman, Sven ^a   De Baecke, Govert ^a   Kenda, Benoît ^a   De Clercq, Pierre J ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

2,6 trans disubstituted piperidines; Alder reaction; Butenolides; Himbacine; Intramolecular Diels; Julia coupling

Indexed keywords

HIMBACINE;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG BINDING; DRUG SYNTHESIS; PLANT; POLYMERIZATION; REACTION ANALYSIS;

EID: 0031800148     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-5928     Document Type: Article

References (57)

1. Brown, R. F. C.; Drummond, R.; Fogerty, A. C.; Hughes, G. K.; Pinhey, J. T.; Ritchie, E.; Taylor, W. C. Aust. J. Chem. 1956, 9, 283.
2. Ritchie, E.; Taylor, W. C. In The Galbulimina Alkaloids; Manske, R. F. H., Ed.; Academic Press: New York, 1967; Vol. 9, p 529.
3. Fridricsons, J.; Mathieson, J. M. Acta Crystallogr. 1962, 15, 119.
4. (a) Kozikowski, A.; Fauq, A. H.; Miller, J. H.; McKinney, M. Bioorg. Med. Chem. Lett. 1992, 2, 797.
5. (b) Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1993, 3, 1247.
6. (c) Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1995, 5, 61.
7. Miller, J. H.; Aagaard, P. J.; Gibson, V. A.; McKinney, M. J. Pharmacol. Exp. Ther. 1992, 263, 663.
8. (a) Hart, D. J.; Wu, W.-L.; Kozikowski, A. P. J. Am. Chem. Soc. 1995, 117, 9369.
9. (b) Hart, D. J.; Li, J.; Wu, W.-L.; Kozikowski, A. P. J. Org. Chem. 1997, 62, 5023.
10. Chackalamannil, S.; Davies, R. J.; Asberom, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812.
11. De Baecke, G.; De Clercq, P. J. Tetrahedron Lett. 1995, 36, 7515.
12. Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, A. T. Tetrahedron Lett. 1995, 36, 9551.
13. Pinhey, J. T.; Ritchie, E.; Taylor, W. C. Aust. J. Chem. 1961, 14, 106.
14. Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 49, 4833.
15. Kocienski, P. J.; Lythgoe, B.; Waterhouse, I. J. Chem. Soc. Perkin Trans. 1 1980, 1045.
16. Chapman, O. L.; Mattes, K. C.; Sheridan, R. S.; Klein, J. A. J. Am. Chem. Soc. 1978, 100, 4878.
17. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
18. Kende, A. S.; Toder, B. H. J. Org. Chem. 1982, 47, 167.
19. (a) Collington, E. W.; Finch, H.; Smith, I. J. Tetrahedron Lett. 1985, 26, 681.
20. (b) Danishefski, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117.
21. Stone, K. J.; Little, J. J. Am. Chem. Soc. 1985, 107, 2495.
22. (a) Bennett, F.; Knight, D.W.; Fenton, G. J. Chem. Soc. Perkin Trans. 1 1991, 519.
23. (b) Stotter, P.L.; Eppner, J.B. Tetrahedron Lett. 1973, 2417.
24. Ibrahim, T.; Grattan T. J.; Whitehurst, J. S. J. Chem. Soc. Perkin Trans. 1 1990, 3317.
25. Jaques, K.; Buda, W. M.; Venema, A.; Sandra, P. J. Microcol. Sep. 1995, 7, 145.
26. Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888.
27. Trost, B. M.; Müller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985.
28. Brookes, M. H.; Golding, B. T.; Howes, D. A.; Hudson, A.T. J. Chem. Soc. Chem. Commun. 1983, 1051.
29. (a) Ashworth, T. V.; Singleton, E.; Hough, J. J. J. Chem. Soc. Dalton Trans. 1977, 1809.
30. (b) Albers, M. O.; Robinson, D. J.; Shaver, A.; Singleton. E. Organometallics 1986, 5, 2199.
31. Trost, B. M.; Calkins, T. L. Tetrahedron Lett. 1995, 36, 6021.
32. (a) Birch, A. J.; Scubba Rao, G. S. R. Tetrahedron Lett. 1968, 3797.
33. (b) Cramer, R J. Am. Chem. Soc. 1966, 88, 2272.
34. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
35. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W.R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
36. For reviews on intramolecular Diels-Alder reactions see: (a) Fallis, A. G. Can. J. Chem. 1984, 62, 183.
37. (b) Brieger, G.; Bennet, J. N. Chem. Rev. 1980, 80, 63.
38. (c) Ciganek, E. Org. React. 1984, 32, 1.
39. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
40. (e) Roush, W. R. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon Press: London, 1991; Vol. 5, p 513.
41. Corey, E. J.; Enders, D.; Bock, M. Tetrahedron Lett. 1976, 7.
42. Gaudemar, M.; Bellasoued M. Tetrahedron Lett. 1990, 31, 349.
43. Still, W. C.; Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Lipton, M.; Liskamp, R.; Chang, G.; Hendrickson, T.; DeGunst, F.; Hasel, W. Macromodel V3.0, Department of Chemistry, Columbia University, New York, NY 10027, USA.
44. Marshall, J. A.; Shearer, B. G.; Crooks, S. L. J. Org. Chem. 1987, 52, 1236.
45. Wang, C.-L. J.; Wuonola, M.A. Org. Prep. Proc. Int. 1992, 24, 583.
46. Wasserman, H. H.; Rusiecki, V. Tetrahedron Lett. 1988, 29, 4977.
47. Ram, S.; Spicer, L. D. Synth. Comm. 1987, 17, 415.
48. Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673.
49. Taber, D. F.; Deker, P. B.; Fales, H. M.; Jones, T. H.; Lloyd, H. A. J. Org. Chem. 1988, 53, 2968.
50. Viaud, M. C.; Rollin, P. Synthesis 1990, 130.
51. Logothetis, A. L. J. Am. Chem. Soc. 1965, 97, 749.
52. Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831.
53. Yang, Y.-L.; Manna, S.; Falck, J.R. J. Am. Chem. Soc. 1984, 106, 3811.
54. (a) Danishefsky, S. J.; Seinick, H. G.; Seinick, R. E.; Zelle, R. E.; DeNinno, M. P. J. Am. Chem. Soc. 1988, 110, 4368.
55. (b) Morzycki, J. W.; Schnoes, H. K.; DeLuca, H. F. J. Org. Chem. 1984, 49, 2148.
56. Achmatowicz, B.; Baranowska, E.; Daniewski, A. R.; Pankowski, J.; Wicha, J. Tetrahedron 1988, 44, 4989.
57. Tabuchi, H.; Hamamoto, T.; Miki, S.; Tejima, T.; Ichihara, A. J. Org. Chem. 1994, 59, 4749.