A short route for the construction of the tetracyclic ring system of silicine-methuenine alkaloids

Tetrahedron Letters

Volumn 37, Issue 20, 1996, Pages 3541-3544

  Bennasar, M Lluïsa ^a   Vidal, Bernat ^a   Lázaro, Angel ^a   Kumar, Rakesh ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029900639     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00607-7     Document Type: Article

References (14)

1. Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340-5341.
2. Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Org. Chem. 1996, in press.
3. Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Org. Chem. 1995, 60, 4280-4286.
4. Joule, J. A. In Indoles, The Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4, pp 232-239.
5. Joule, J. A. In Indoles, The Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4, pp 232-239.
6. (b) Alvarez, M.; Joule, J. In Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Vol. 25, Supplement to Part 4, pp 234-236.
7. (b) Alvarez, M.; Joule, J. In Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Vol. 25, Supplement to Part 4, pp 234-236.
8. Husson, H.-P.; Bannai, K.; Freire, R.; Mompon, B.; Reis, F. A. M. Tetrahedron 1978, 34, 1363-1368.
9. For the synthesis of a model tetracyclic structure, see: Grierson, D. S.; Bettiol, J.-L.; Buck, I.; Husson, H.-P.; Rubiralta, M.; Díez, A. J. Org. Chem. 1992, 57, 6414-6421.
10. 5: C, 65.61; H, 6.29; N, 7.29. Found: C, 65.60; H, 6.41; N, 7.12.
11. 5 412.1998, found 412.2017.
12. 4: C, 68.46; H, 6.57; N, 7.60. Found: C, 68.47; H, 6.57; N, 7.61.
13. 4: C, 67.45; H, 5.36; N, 8.28. Found: C, 67.56; H, 5.39; N, 8.08.
14. 4 380.1736, found 380.1745.