New asymmetric routes to ajmaline and suaveoline indole alkaloids

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 21, 2000, Pages 3566-3577

  Bailey, Patrick D ^a   Morgan, Keith M ^a   Smith, David I ^b   Vernon, John M ^c  

^a HERIOT WATT UNIVERSITY   (United Kingdom)

^b Sanofi Synthelabo Inc   (United Kingdom)

^c UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; PROTONS; REDUCTION; STEREOCHEMISTRY; SURFACE TREATMENT; SYNTHESIS (CHEMICAL);

CYCLIZATION; INTRAMOLECULAR ROUTES;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 0034619644     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b005694o     Document Type: Article

References (30)

1. S. F. Martin, C. W. Clark and J. W. Corbett, J. Org. Chem., 1995, 60, 3236.
2. A. Jossang, P. Fodor and B. Bodo, J. Org. Chem., 1998, 63, 7162 and references therein.
3. J. Li and J. M. Cook, J. Org. Chem., 1998, 63, 4166.
4. S. P. Majumbar, P. Potier and J. Poissen, Tetrahedron Lett., 1972, 1563.
5. (a) M. A. Amer and W. E. Court, Phytochemistry, 1981, 20, 2569;
6. (b) A. M. A. G. Nasser and W. E. Court, Phytochemistry, 1983, 22, 2297.
7. (a) S. Enders, H. Takayama, S. Suda, M. Kitajima, N. Aimi, S. Sakai and J. Stockigt, Phytochemistry, 1993, 32, 725;
8. (b) L. Polz, J. Stockigt, H. Takayama, N. Uchida, N. Aimi and S. Sakai, Tetrahedron Lett., 1990, 31, 6693.
9. M. L. Trudell and J. M. Cook, J. Am. Chem. Soc., 1989, 111, 7504.
10. P. Yu and J. M. Cook, J. Org. Chem., 1998, 63, 9160.
11. X. Fu and J. M. Cook, J. Am. Chem. Soc., 1992, 114, 6910.
12. P. D. Bailey and N. R. McLay, J. Chem. Soc., Perkin Trans. 1, 1993, 441.
13. P. D. Bailey, S. P. Hollinshead, N. R. McLay, K. M. Morgan, S. J. Palmer, S. N. Prince, C. D. Reynolds and S. D. Wood, J. Chem. Soc., Perkin Trans. 1, 1993, 431. /
14. P. D. Bailey, I. D. Collier, S. P. Hollinshead, M. H. Moore, K. M. Morgan, D. I. Smith and J. M. Vernon, J. Chem. Soc., Perkin Trans. 1, 1997, 1209.
15. S. P. Hollinshead, DPhil Thesis, York, 1987.
16. (a) X. Fu and J. M. Cook, J. Org. Chem., 1993, 58, 661;
17. (b) D. Soerens, PhD Thesis, University of Wisconsin-Milwaukee, 1978;
18. (c) R. W. Weber, PhD Thesis, University of Wisconsin-Milwaukee, 1985.
19. Y. Horiguchi, S. Matsuzawa, E. Nakamura and I. Kuwajima, Tetrahedron Lett., 1986, 27, 4025.
20. P. D. Bailey, S. P. Hollinshead, M. H. Moore, K. M. Morgan, D. I. Smith and J. M. Vernon, Tetrahedron Lett., 1994, 35, 3585.
21. (a) B. H. Han and P. Boudjouk, J. Org. Chem., 1982, 47, 5030;
22. (b) A. K. Bose, K. Gupta and M. S. Manhas, J. Chem. Soc., Chem. Commun., 1984, 86;
23. (c) T. Kitazume, Synthesis, 1985, 855.
24. (a) E. Erdik, Tetrahedron, 1987, 43, 2203;
25. (b) C. Rene, A. Furstner and H. Weidmann, J. Chem. Soc., Chem. Commun., 1986, 775.
26. W. Zwanenburg, Tetrahedron Lett., 1970, 935.
27. E. N. Zil'berman, Russ. Chem. Rev., 1984, 53, 900.
28. R. Grigg, T. R. B. Mitchell and S. Sutthivaiyakit, Tetrahedron Lett., 1979, 1067.
29. P. D. Bailey, P. J. Cochrane, F. Irvine, K. M. Morgan, D. J. Pearson and K. T. Veal, Tetrahedron Lett., 1999, 40, 4593.
30. P. D. Bailey, K. M. Morgan, G. M. Rosair and R. LI. Thomas, Tetrahedron Lett., 1999, 40, 8255.