Synthesis of chiral 2′,3′-pyranone(pyrrolidinone)-fused tryptamines

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 221-223

  Dardennes, Emmanuel ^a   Kovács Kulyassa, Árpád ^a   Renzetti, Andrea ^a   Sapi, Janos ^a   Laronze, Jean Yves ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Chiral tryptamine derivatives; Diastereoselective synthesis; Garner's aldehyde; Multicomponent reaction; Trimolecular condensation

Indexed keywords

ACID; ALDEHYDE; INDOLE; KETONE DERIVATIVE; TRYPTAMINE DERIVATIVE;

ARTICLE; CHROMATOGRAPHY; ENANTIOSELECTIVITY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037421085     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02537-6     Document Type: Article

References (17)

1. Nemes C., Jeannin L., Sapi J., Laronze M., Seghir H., Augé F., Laronze J.-Y. Tetrahedron. 56:2000;5479-5492.
2. Boisbrun M., Kovács-Kulyassa Á., Jeannin L., Sapi J., Toupet L., Laronze J.-Y. Tetrahedron Lett. 41:2000;9771-9775.
3. For some fused tryptamine derivatives, see: (a) Macor, J. E.; Ryan, K. Heterocycles 1990, 31, 1497-1504; (b) Schlecht, M. F.; Tsaroushtsis, D.; Lipovac, M. N.; Debler, E. A. J. Med. Chem. 1990, 33, 386-394; (c) Ghosh, A.; Wang, W.; Freeman, J. P.; Althaus, J. S.; Von Voigtlander, P. F.; Scahill, T. A.; Mizsak, S. A; Szmuszkovicz, J. Tetrahedron 1991, 47, 8653-8662; (d) Ezquerra, J.; Pedregal, C.; Lamas, C.; Pastor, A.; Alvarez, P.; Vaquero, J. J. Tetrahedron Lett. 1996, 37, 683-686.
4. For some fused tryptamine derivatives, see: (a) Macor, J. E.; Ryan, K. Heterocycles 1990, 31, 1497-1504; (b) Schlecht, M. F.; Tsaroushtsis, D.; Lipovac, M. N.; Debler, E. A. J. Med. Chem. 1990, 33, 386-394; (c) Ghosh, A.; Wang, W.; Freeman, J. P.; Althaus, J. S.; Von Voigtlander, P. F.; Scahill, T. A.; Mizsak, S. A; Szmuszkovicz, J. Tetrahedron 1991, 47, 8653-8662; (d) Ezquerra, J.; Pedregal, C.; Lamas, C.; Pastor, A.; Alvarez, P.; Vaquero, J. J. Tetrahedron Lett. 1996, 37, 683-686.
5. For some fused tryptamine derivatives, see: (a) Macor, J. E.; Ryan, K. Heterocycles 1990, 31, 1497-1504; (b) Schlecht, M. F.; Tsaroushtsis, D.; Lipovac, M. N.; Debler, E. A. J. Med. Chem. 1990, 33, 386-394; (c) Ghosh, A.; Wang, W.; Freeman, J. P.; Althaus, J. S.; Von Voigtlander, P. F.; Scahill, T. A.; Mizsak, S. A; Szmuszkovicz, J. Tetrahedron 1991, 47, 8653-8662; (d) Ezquerra, J.; Pedregal, C.; Lamas, C.; Pastor, A.; Alvarez, P.; Vaquero, J. J. Tetrahedron Lett. 1996, 37, 683-686.
6. For some fused tryptamine derivatives, see: (a) Macor, J. E.; Ryan, K. Heterocycles 1990, 31, 1497-1504; (b) Schlecht, M. F.; Tsaroushtsis, D.; Lipovac, M. N.; Debler, E. A. J. Med. Chem. 1990, 33, 386-394; (c) Ghosh, A.; Wang, W.; Freeman, J. P.; Althaus, J. S.; Von Voigtlander, P. F.; Scahill, T. A.; Mizsak, S. A; Szmuszkovicz, J. Tetrahedron 1991, 47, 8653-8662; (d) Ezquerra, J.; Pedregal, C.; Lamas, C.; Pastor, A.; Alvarez, P.; Vaquero, J. J. Tetrahedron Lett. 1996, 37, 683-686.
7. For some selected 3,4-annulated (tetrahydro)-β-carbolines, see: (a) Dubois, L.; Dorey, G.; Potier, P.; Dodd, R. H. Tetrahedron: Asymmetry 1995, 6, 455-462; (b) Nyerges, M.; Rudas, M.; Bitter, I.; Toke, L.; Szántay, C., Jr. Tetrahedron 1997, 53, 3269-3280; (c) Ezquerra, J.; Pedregal, C.; Lamas, C.; Pastor, A.; Alvarez, P.; Vaquero, J. J. Tetrahedron 1997, 53, 8237-8248; (d) Teller, S.; Eluwa, S.; Koller, M.; Uecker, A.; Beckers, T.; Baasner, S.; Böhmer, F.-D.; Mahboobi, S. Eur. J. Med. Chem. 2000, 35, 413-427.
8. For some selected 3,4-annulated (tetrahydro)-β-carbolines, see: (a) Dubois, L.; Dorey, G.; Potier, P.; Dodd, R. H. Tetrahedron: Asymmetry 1995, 6, 455-462; (b) Nyerges, M.; Rudas, M.; Bitter, I.; Toke, L.; Szántay, C., Jr. Tetrahedron 1997, 53, 3269-3280; (c) Ezquerra, J.; Pedregal, C.; Lamas, C.; Pastor, A.; Alvarez, P.; Vaquero, J. J. Tetrahedron 1997, 53, 8237-8248; (d) Teller, S.; Eluwa, S.; Koller, M.; Uecker, A.; Beckers, T.; Baasner, S.; Böhmer, F.-D.; Mahboobi, S. Eur. J. Med. Chem. 2000, 35, 413-427.
9. For some selected 3,4-annulated (tetrahydro)-β-carbolines, see: (a) Dubois, L.; Dorey, G.; Potier, P.; Dodd, R. H. Tetrahedron: Asymmetry 1995, 6, 455-462; (b) Nyerges, M.; Rudas, M.; Bitter, I.; Toke, L.; Szántay, C., Jr. Tetrahedron 1997, 53, 3269-3280; (c) Ezquerra, J.; Pedregal, C.; Lamas, C.; Pastor, A.; Alvarez, P.; Vaquero, J. J. Tetrahedron 1997, 53, 8237-8248; (d) Teller, S.; Eluwa, S.; Koller, M.; Uecker, A.; Beckers, T.; Baasner, S.; Böhmer, F.-D.; Mahboobi, S. Eur. J. Med. Chem. 2000, 35, 413-427.
10. For some selected 3,4-annulated (tetrahydro)-β-carbolines, see: (a) Dubois, L.; Dorey, G.; Potier, P.; Dodd, R. H. Tetrahedron: Asymmetry 1995, 6, 455-462; (b) Nyerges, M.; Rudas, M.; Bitter, I.; Toke, L.; Szántay, C., Jr. Tetrahedron 1997, 53, 3269-3280; (c) Ezquerra, J.; Pedregal, C.; Lamas, C.; Pastor, A.; Alvarez, P.; Vaquero, J. J. Tetrahedron 1997, 53, 8237-8248; (d) Teller, S.; Eluwa, S.; Koller, M.; Uecker, A.; Beckers, T.; Baasner, S.; Böhmer, F.-D.; Mahboobi, S. Eur. J. Med. Chem. 2000, 35, 413-427.
11. Garner P., Park J.M. J. Org. Chem. 52:1987;2361-2364.
12. Dondoni A., Perrone D. Org. Synth. 77:1999;64-77.
13. Evans P.A., Holmes A.B., Russell K. J. Chem Soc., Perkin Trans. 1. 1994;3397-3408.
14. Oikawa Y., Hirasawa O., Yonemitsu O. Tetrahedron Lett. 19:1978;1759.
15. 6, 343 K): δ 1.20 (s, 3H), 1.47 (s, 3H), 1.71 (s, 9H), 1.83 (s, 3H), 2.05 (s, 3H), 4.17 (dd, 1H, J=9.3, 6.3 Hz), 4.46 (s, 1H), 4.98 (brs, 1H), 5.12 (brs, 1H), 5.34 (d, 1H, J=4.0 Hz), 7.38-7.52 (m, 4H), 7.86 s, 1H), 8.32 (d, 1H, J=5.2 Hz).
16. 6): δ 1.26 (s, 9H), 3.51 (s, 3H), 3.95 (dd, 1H, J=11.6, 8.6 Hz), 4.22 (d, 1H, J=11.6 Hz), 4.30-4.38 (m, 2H), 4.63 (dd, 1H, J=10.8, 3.8 Hz), 6.46 (d, 1H, J=7.2 Hz), 7.03 (t, 1H, J=7.9 Hz), 7.11 (t, 1H, J=7.9 Hz), 7.31 (d, 1H, J=2.3 Hz), 7.39 (d, 1H, J=7.9 Hz), 7.70 (d, 1H, J=7.9 Hz), 10.23 (brs, 1H).
17. 3): δ -0.13 (s, 6H), 0.81 (s, 9H), 2.23 (brs, 2H), 3.26 (m, 2H), 3.70 (dd, 1H, J=11.1 and 8.0 Hz), 3.90 (m, 1H), 3.98 (d, 1H, J=11.1 Hz), 6.58 (brs, 1H), 7.05-7.25 (m, 3H), 7.37 (d, 1H, J=7.9 Hz), 7.51 d, 1H, J=7.8 Hz), 8.93 (brs, 1H).