Synthesis of the tangutorine skeleton

Tetrahedron Letters

Volumn 40, Issue 39, 1999, Pages 7119-7122

  Berner, Mathias ^a   Tolvanen, Arto ^a   Jokela, Reija ^a  

^a AALTO UNIVERSITY   (Finland)

Author keywords

amino nitrile; Conformation; Epimerization; Indole alkaloid

Indexed keywords

TANGUTORINE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; FINLAND; OXIDATION REDUCTION REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033600766     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01474-4     Document Type: Article

References (19)

1. 1. Lounasmaa, M.; Jokela, R. Tetrahedron 1990, 46,615-622.
2. 2. Lounasmaa, M.; Din Belle, D.; Tolvanen, A. Tetrahedron 1998, 54, 4673-4678.
3. 3. Biogenetic numbering: Le Men, J.; Taylor, W. I. Experientia 1965, 21, 508-510. We propose the numbering depicted in 1.
4. 4. Duan, J.-A.; Williams, I. D.; Che, C.-T.; Zhou, R.-H.; Zhao, S.-X. Tetrahedron Lett. 1999, 40, 2593-2596.
5. 5. Khuyen, N. N. Tap Chi Hoa Hoc 1977, 15, 27-31; Chem. Abstr. 1979, 90, 168477.
6. 5. Khuyen, N. N. Tap Chi Hoa Hoc 1977, 15, 27-31; Chem. Abstr. 1979, 90, 168477.
7. 6. Shut, R. N. U. S. Patent 3 087 930, 1963; Chem. Abstr. 1963, 59, 11497f.
8. 6. Shut, R. N. U. S. Patent 3 087 930, 1963; Chem. Abstr. 1963, 59, 11497f.
9. 7. Fry, E. M. J. Org. Chem. 1964, 29, 1647-1650.
10. 8. Vierhapper, F. W.; Eliel, E. L. J. Org. Chem. 1975, 40, 2729-2734.
11. 9. Yields of the Fry reaction and especially the cyclization are unoptimized.
12. 13C NMR: δ 67.1 (C-19), 60.6 (C-3), 41.5 (C-20), 22.1(C-6).
13. 11. For a review, see: Lounasmaa, M.; Berner, M.; Tolvanen, A. Heterocycles 1998, 48, 1275-1290.
14. 1H NMR integration. Yields in epimerization reactions were nearly quantitative.
15. 13C NMR: δ 58.6 (C-19), 57.1 (C-3), 40.0 (C-20), 16.2 (C-6).
16. 14. (a) Gobble, G. W.; Nelson, R. B. J. Org. Chem. 1973, 38, 2831-2834;
17. (b) Gribble, G. W.; Nelson, R. B.; Johnson, J. L; Levy, G. C. J. Org. Chem. 1975, 40, 3720-3725. See also: Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645-3655 (note 55).
18. (b) Gribble, G. W.; Nelson, R. B.; Johnson, J. L; Levy, G. C. J. Org. Chem. 1975, 40, 3720-3725. See also: Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645-3655 (note 55).
19. 15. Lounasmaa, M. Curr. Org. Chem. 1998, 2, 63-90, and references therein.