Daphniphyllum Alkaloids. 14. Total Synthesis of (±)-Bukittinggine

Journal of Organic Chemistry

Volumn 57, Issue 9, 1992, Pages 2575-2585

  Heathcock, Clayton H ^a   Stafford, Jeffrey A ^a   Clark, David L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001192457     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00035a011     Document Type: Article

References (43)

1. Heathcock, C. H.; Stafford, J. A. J. Org. Chem., preceding paper in this issue
2. Arbain, D.; Byrne, L. T.; Cannon, J. R.; Patrick, V. A.; White, A. H. Aust. J. Chem. 1990, 43, 185
3. Yamamura, S.; Hirata, Y. In The Alkaloids; Manske, R. H. F., Ed.; Academic: New York, 1975; Vol. 15, p 41
4. Yamamura, S.; Hirata, Y. Int. Rev. Sci., Org. Chem., Ser. 2 1976, 9, 161
5. Yamamura, S. In The Alkaloids; Brossi, A., Ed.; Academic: New York, 1986; Vol. 29, p 265
6. “tetracyclization reaction”, part 11 in this series: Heathcock, C. H.; Hansen, M. M.; Ruggeri, R. B.; Kath, J. C. J. Org. Chem., second paper in the series in this issue
7. Ruggeri, R. B.; Hansen, M. M.; Heathcock, C. H. J. Am. Chem. Soc. 1988, 110, 8734
8. Anderson, R. J.; Corbin, V. L.; Cotterrell, G.; Cox, G. R.; Henrick, C. A.; Schaub, F.; Siddall, J. B. J. Am. Chem. Soc. 1975, 97, 1197
9. Poulter, C. D.; Wiggins, P. L.; Plummer, T. L. J. Org. Chem. 1981, 46, 1532
10. Leopold, E. J. Org. Synth. 1985, 64, 164
11. Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849
12. Mukhopadhyay, T.; Seebach, D. Helv. Chem. Acta 1982, 65, 385
13. Huang, S. L.; Omura, K.; Swern, D. J. Org. Chem. 1976, 41, 3329
14. Mancuso, A. J.; Swern, D. Synthesis 1981, 165
15. Overman, L. E.; Ricca, D. J. In “Intramolecular Mannich and Related Reactions,” Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon: Oxford, 1991
16. Marson, C. M.; Grabowska, U.; Walsgrove, T.; Eggleston, D. S.; Baures, P. W. J. Org. Chem. 1991, 56, 2603
17. Heathcock, C. H.; Piettre, S.; Kath, J. Pure Appl. Chem. 1990, 62, 1911
18. Heathcock, C. H.; Piettre, S.; Ruggeri, R. B.; Ragan, J. A.; Kath, J. C. J. Org. Chem., third paper in the series in this issue
19. Horiuchi, C. A.; Satoh, J. Y. J. Chem. Soc., Perkin Trans. 1 1982, 2595
20. McMurry, J. E.; Kocovsky, P. Tetrahedron Lett. 1984, 25, 4187
21. Trost, B. M.; Genet, J. P. J. Am. Chem. Soc. 1976, 98, 8516
22. Trost, B. M.; Cossy, J. J. Am. Chem. Soc. 1982, 104, 6881
23. Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800
24. Trost, B. M.; Metzner, P. J. J. Am. Chem. Soc. 1980, 102, 3572
25. Huttel, R. Synthesis 1970, 225
26. Trost, B. M. Tetrahedron 1977, 33, 2615
27. Hegedus, L. S. Tetrahedron 1984, 40, 2415.
28. Brown, M.; Piszkiewicz, L. W. J. Org. Chem. 1967, 32, 2013
29. Djerassi, C.; Gutzwiller, J. J. Am. Chem. Soc. 1966, 88, 4537
30. Hoffman, J. M.; Schlessinger, R. H. J. Chem. Soc., Chem. Commun. 1971, 1245
31. Brown, H. C.; Murray, K. J. Am. Chem. Soc. 1959, 81, 4108
32. Hart, D. W.; Schwartz, J. J. Am. Chem. Soc. 1974, 96, 8115
33. House, H. O. Modern Synthetic Reactions, 2nd ed.; Benjamin/Cummings: Menlo Park, 1972; pp 19-23
34. Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G. J. Chem. Soc. A 1966, 1711
35. Jardine, F. H.; Osborn, J. A.; Wilkinson, G. J. Chem. Soc. A 1967, 1574
36. Rylander, P. N. Catalytic Hydrogenation over Platinum Metals; Academic Press: New York, 1967; pp 89-107
37. Kabalka, G. W.; Shoup, T. M.; Goudgaon, N. M. J. Org. Chem. 1989, 54, 5930
38. Krishnamurthy, S.; Brown, H. C. J. Org. Chem. 1976, 41, 3064
39. Reist, E. J.; Bartuska, V. J.; Goodman, L. J. Org. Chem. 1964, 29, 3725
40. Villalobos, A.; Danishefsky, S. J. J. Org. Chem. 1990, 55, 2776
41. Fetizon, M.; Golfier, M.; Louis, J.-M. J. Chem. Soc., Chem. Commun. 1969, 1118
42. Fetizon, M.; Golfier, M.; Louis, J.-M. Tetrahedron 1975, 171
43. McKillop, A.; Young, D. W. Synthesis 1979, 401