Total syntheses of (±)-cryptopleurine, (±)-antofine and (±)- deoxypergularinine

Tetrahedron

Volumn 55, Issue 9, 1999, Pages 2659-2670

  Lebrun, Stéphane ^a   Couture, Axel ^a   Deniau, Eric ^a   Grandclaudon, Pierre ^a  

^a CNRS   (France)

Author keywords

Alkaloids; Amines; Cyclization; Enecarbamates

Indexed keywords

ALKALOID; ANTOFINE; CARBAMIC ACID DERIVATIVE; CRYPTOPLEURINE; DEOXYPERGULARININE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; PHYTOCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0033605308     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00017-4     Document Type: Article

References (48)

1. Bick, I. R. C.; Sinchai, W. In: The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 19; pp. 193-220.
2. Gellert, E. J. Nat. Prod. 1982, 45, 50-73.
3. Suffness, M.; Cordell, G. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1985; Vol. 25; p. 156.
4. Suffness, M.; Cordell, G. A. In The Alkaloids, Brossi, A., Ed.; Academic Press: Orlando, 1985; Vol. 25; pp. 3-355.
5. Gellert, E.; Rudzats, R. J. Med. Chem. 1964, 7, 361-362.
6. Duan, J.; Yu, L. Zhongcaoyao 1991, 22, 316-318; Chem. Abstr. 1992, 116, 386.
7. Duan, J.; Yu, L. Zhongcaoyao 1991, 22, 316-318; Chem. Abstr. 1992, 116, 386.
8. Cuifolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082-12089 and references cited therein.
9. Govindachari, T. R. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, 517-588.
10. Govindachari, T. R.; Viswanathan, N. Heterocycles 1978, 11, 587-613.
11. Paton, J. M.; Pauson, P. L.; Stevens, T. S. J. Chem. Soc. C 1969, 1309-1314.
12. Kotani, E.; Kitazawa, M.; Tobinaga, S. Tetrahedron 1974, 30, 3023-3029.
13. Herbert, R. B. J. Chem. Soc., Chem. Commun. 1978, 794-795.
14. Crag, J. E.; Herbert, R. B. J. Chem. Soc., Perkin Trans. 1 1982, 2487-2490.
15. Iida, H.; Kibayashi, C. Tetrahedron Lett. 1981, 22, 1913-1914.
16. Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412-2418.
17. Bremmer; M. L.; Khatri, N. A.; Weinreb, S. M. J. Org. Chem. 1983, 48, 3661-3666.
18. Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; de Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955-1962.
19. Grieco, P. A.; Parker, D. J. Org. Chem. 1988, 53, 3325-3330.
20. Govindachari, T. R.; Ragade, I. S.; Viswanathan, N. J. Chem. Soc. 1962, 1357-1360.
21. Wiegrebe, W.; Faber, L.; Brockmann, H.; Budzikiewicz, H.; Krüger, U. Liebigs Ann. Chem. 1969, 721, 154-162.
22. Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503-2516.
23. Wiegrebe, W.; Faber, L.; Budzikiewicz, H. Liebigs Ann. Chem. 1970, 733, 125-140.
24. Cragg, J. E.; Herbert, R. B.; Jackon, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477-2485.
25. Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1995, 36, 935-936.
26. Suzuki, H.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1995, 60, 6114-6122.
27. Buckley III, T. F.; Rapoport, H. J. Org. Chem. 1983, 48, 4222-4232.
28. Faber, L.; Wiegrebe, W. Helv. Chim. Acta 1976, 59, 2201-2212.
29. de la Lande, I. S. Australian J. Exp. Biol. Med. Sci. 1948, 26, 181-187.
30. Gellert, E.; Riggs, N. V. Aust. J. Chem. 1954, 7, 113-119.
31. Hart, N. K.; Johns, S. R.; Lamberton, J. A. Aust. J. Chem. 1968, 21, 2579-2581.
32. Cavé, A.; Leboeuf, M.; Moskourtz, H.; Ranaivo, A.; Bick, I.; Ralph, C. Aust. J. Chem. 1989, 42, 2243-2263.
33. Mulchandani, N. B.; Venkatachalam, S. R. Phytochemistry 1976, 15, 1561-1563.
34. Couture, A.; Deniau, E.; Hoarau, C.; Grandclaudon, P. J. Org. Chem. 1998, 63, 3128-3132.
35. Couture, A; Deniau, E.; Grandclaudon, P.; Woisel, P. Tetrahedron 1996, 52, 4433-4448.
36. Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron 1997, 53, 10313-10330.
37. Couture, A.; Deniau, E.; Grandclaudon, P.; Woisel, P.; Carpentier, J.-F. Tetrahedron Lett. 1996, 37, 3697-3700.
38. Couture, A.; Deniau, E.; Lebrun, S.; Grandclaudon, P. J. Chem. Soc., Perkin Trans, 1 1998, 1403-1407.
39. Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 60, 196-201.
40. Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron: Asymmetry 1991, 2, 51-62.
41. Noyori, R.; Ohkuma, T.; Kitamura, K.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856-5858.
42. James, B. R. Homogeneous Hydrogenation; Wiley: New York, 1973.
43. Dieter, R. K.; Sharma, R. R. J. Org. Chem. 1996, 61, 4180-4184.
44. Bremmer, M. L.; Khatri, N. A.; Weinreb, S. M. J. Org. Chem. 1983, 48, 3661-3666.
45. Cassaday, J. T.; Bogert, M. T. J. Am. Chem. Soc. 1939, 61, 2461-2462.
46. Bradsher, C. K.; Berger, H. J. Am. Chem. Soc. 1957, 80, 930-932.
47. Foldrak, S. Tetrahedron 1971, 27, 3465-3476.
48. Govindachari, T. R. Tetrahedron 1961, 14, 288-295.