Synthesis of aspidospermidine alkaloids from 1,2,3,4- tetrahydrocarbazole: Total stereoselective synthesis of (±)-18- noraspidospermidine

Tetrahedron

Volumn 55, Issue 36, 1999, Pages 11095-11108

  Urrutia, Anahí ^a   Rodríguez, J Gonzalo ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

( ) 18 Noraspidospermidine; Indolisation; Nickel boride; Stereoselective reduction; Tetrahydrocarbazolones

Indexed keywords

1,2,3,4 TETRAHYDROCARBAZOLE DERIVATIVE; 18 NORASPIDOSPERMIDINE; ALKALOID; ASPIDOSPERMINE; CYCLOHEXANONE DERIVATIVE; NICKEL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DESULFURIZATION; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033520255     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00614-6     Document Type: Article

References (24)

1. The Monoterpenoids Indole Alkaloids: Saxton, J. E. The Chemistry of Heterocyclic Compounds; John Wiley and Sons, Inc., New York, 1983, Vol. 25, Part 4, pp 330-437, Suppl. 1994. Aspidosperma alkaloids: Cordell, G. A. and Saxton, J. E. in The Alkaloids, Manske, R. H. F. and Rodrigo, R. G. A., Eds. Academic Press, New York, 1981, Vol. 20. pp 132-280.
2. The Monoterpenoids Indole Alkaloids: Saxton, J. E. The Chemistry of Heterocyclic Compounds; John Wiley and Sons, Inc., New York, 1983, Vol. 25, Part 4, pp 330-437, Suppl. 1994. Aspidosperma alkaloids: Cordell, G. A. and Saxton, J. E. in The Alkaloids, Manske, R. H. F. and Rodrigo, R. G. A., Eds. Academic Press, New York, 1981, Vol. 20. pp 132-280.
3. Saxton, J. E. Nat. Prod. Rep. 1994, 11, 493.
4. Rodríguez, J. G.; Temprano, F.; Esteban-Calderón, C.; Martinez-Ripoll, M. J. Chem. Soc. Perkin Trans. I 1989, 2117-2121.
5. Rodríguez, J. G.; del Valle, C; Esteban-Calderón, C.; Martinez-Ripoll, M. J. Chem. Cryst. 1995, 25, 249-257.
6. Patir, S.; Götz, P. H. Liebigs Ann. Chem. 1993, 1323-1325.
7. Forns, P; Diez, A; Rubiralta, M. J. Org. Chem. 1996, 61, 7882-7888.
8. D'Angelo, J.; Desmaële, D. Tetrahedron Lett. 1990, 31, 879-882; ibid, 1990, 31, 883-886.
9. D'Angelo, J.; Desmaële, D. Tetrahedron Lett. 1990, 31, 879-882; ibid, 1990, 31, 883-886.
10. Abrahamson, H. B. Organometallics 1984, 3, 1379-1382.
11. Stork, G.; Dolfini, J.E. J. Am. Chem. Soc. 1963, 85, 2872-2873. Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1965, 2261. Stevens, R. V.; Fitzpatrick, J. M.; Kaplan, M.; Zimmerman, D. L. J. Chem. Soc. Chem. Comm. 1971, 857-858.
12. Stork, G.; Dolfini, J.E. J. Am. Chem. Soc. 1963, 85, 2872-2873. Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1965, 2261. Stevens, R. V.; Fitzpatrick, J. M.; Kaplan, M.; Zimmerman, D. L. J. Chem. Soc. Chem. Comm. 1971, 857-858.
13. Stork, G.; Dolfini, J.E. J. Am. Chem. Soc. 1963, 85, 2872-2873. Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1965, 2261. Stevens, R. V.; Fitzpatrick, J. M.; Kaplan, M.; Zimmerman, D. L. J. Chem. Soc. Chem. Comm. 1971, 857-858.
14. Azzonzi, A.; Perrin B.; Sinibaldi M.E; Gramain J.C. Tetrahedron Lett. 1993, 34, 5451-5454. J.C. Gramain, H.P. Husson, Y. Troin, J. Org. Chem. 1985, 50, 5517-5520. J.C. Gramain, H.P. Husson, Y. Troin, J. Org. Chem. 1985, 50, 5517-5520.
15. Azzonzi, A.; Perrin B.; Sinibaldi M.E; Gramain J.C. Tetrahedron Lett. 1993, 34, 5451-5454. J.C. Gramain, H.P. Husson, Y. Troin, J. Org. Chem. 1985, 50, 5517-5520.
16. Desmaële. D.; D'Angelo, J. J. Org. Chem. 1994, 59, 2292-2303, and references cited therein.
17. Urrutia, A.; Rodríguez, J.G. Tetrahedron Lett. 1998, 39, 4143-4146.
18. Canoira, L.; Rodríguez, J. G.; Subirats, J. B. Eur. J. Med. Chem. 1989, 24, 39-44.
19. Lloyd, D. H.; Nichols, D. E. J. Org. Chem. 1986, 51, 4294-4295; Han, B. H.; Shin, D. H.; Cho, S.Y. Tetrahedron Lett. 1985, 50, 6233-6234. Okamoto, Y.; Nitta, Y.; Imanaka, T.; Teranishi, S. J. Chem. Soc., Faraday Trans, 1, 75, 2027, 1979. Ganem, B.; Osby, J. O. Chem. Rev. 1986, 86, 764.
20. Lloyd, D. H.; Nichols, D. E. J. Org. Chem. 1986, 51, 4294-4295; Han, B. H.; Shin, D. H.; Cho, S.Y. Tetrahedron Lett. 1985, 50, 6233-6234. Okamoto, Y.; Nitta, Y.; Imanaka, T.; Teranishi, S. J. Chem. Soc., Faraday Trans, 1, 75, 2027, 1979. Ganem, B.; Osby, J. O. Chem. Rev. 1986, 86, 764.
21. Lloyd, D. H.; Nichols, D. E. J. Org. Chem. 1986, 51, 4294-4295; Han, B. H.; Shin, D. H.; Cho, S.Y. Tetrahedron Lett. 1985, 50, 6233-6234. Okamoto, Y.; Nitta, Y.; Imanaka, T.; Teranishi, S. J. Chem. Soc., Faraday Trans, 1, 75, 2027, 1979. Ganem, B.; Osby, J. O. Chem. Rev. 1986, 86, 764.
22. Lloyd, D. H.; Nichols, D. E. J. Org. Chem. 1986, 51, 4294-4295; Han, B. H.; Shin, D. H.; Cho, S.Y. Tetrahedron Lett. 1985, 50, 6233-6234. Okamoto, Y.; Nitta, Y.; Imanaka, T.; Teranishi, S. J. Chem. Soc., Faraday Trans, 1, 75, 2027, 1979. Ganem, B.; Osby, J. O. Chem. Rev. 1986, 86, 764.
23. Gallagher, T.; Magnus, P.; Huffman, J. C. J. Am. Chem. Soc. 1983, 105, 4750-4757.
24. Magnus. P.; Sear, N. L.; Kim, Ch. S.; Vicker. N. J. Org. Chem. 1992, 57, 70-78.