A brief total synthesis of eupolauramine

Synlett

Volumn , Issue 12, 2004, Pages 2233-2235

  Rys, Veronique ^a   Couture, Axel ^a   Deniau, Eric ^a   Lebrun, Stéphane ^a   Grandclaudon, Pierre ^a  

^a UNIV LILLE   (France)

Author keywords

Alkaloids; Carbanions; Enols; Ring closure; Total synthesis

Indexed keywords

ALKALOID; AZAISOINDOLINONE; EUPOLAURAMINE; FREE RADICAL; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; EXTRACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 5644257230     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-830889     Document Type: Article

References (23)

1. Carroll, A. R.; Taylor, W. C. Aust. J. Chem. 1991, 44, 1615.
2. Bowden, B. F.; Ritchie, E.; Taylor, W. C. Aust. J. Chem. 1972, 25, 2659.
3. (a) Shamma, M.; Moniot, J.-L. Isoquinoline Alkaloids Research 1972-1977; Plenum Press: New York, 1978, 393-394.
4. (b) Mix, D. B.; Guinaudeau, H.; Shamma, M. J. Nat. Prod. 1982, 45, 657.
5. Kawase, M.; Yuko, M.; Sakamoto, T.; Shimada, M.; Kikugawa, Y. Tetrahedron 1989, 45, 1653.
6. Kikugawa, Y.; Kawase, M.; Yuko, M.; Sakamoto, T.; Shimada, M. Tetrahedron Lett. 1988, 29, 4297.
7. Levin, J. I.; Weinreb, S. M. J. Org. Chem. 1984, 49, 4325.
8. Levin, J. I.; Weinreb, S. M. J. Am. Chem. Soc. 1983, 105, 1397.
9. Karuso, P.; Taylor, W. C. Aust. J. Chem. 1984, 37, 1271.
10. Kitahara, Y.; Mochii, M.; Mori, M.; Kubo, A. Tetrahedron 2003, 59, 2885.
11. Hoarau, C.; Couture, A.; Cornet, H.; Deniau, E.; Grandclaudon, P. J. Org. Chem. 2001, 66, 8064.
12. Goehring, R. R. Tetrahedron Lett. 1992, 33, 6045.
13. Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev. 1998, 98, 409.
14. (a) Katritzky, A. R.; Yang, Z.; Lam, J. N. J. Org. Chem. 1991, 56, 6917.
15. (b) Katritzky, A. R.; Qi, M. Tetrahedron 1998, 54, 2647.
16. (c) Katritzky, A. R.; Qi, M.; Feng, D.; Nichols, D. A. J. Org. Chem. 1997, 62, 4121.
17. (a) Katritzky, A. R.; Ignatchenko, A. V.; Lang, H. J. Org. Chem. 1995, 60, 4002.
18. (b) Katritzky, A. R.; Ignatchenko, A. V.; Lang, H. Synth. Commun. 1995, 25, 1197.
19. (c) Deniau, E.; Enders, D. Tetrahedron Lett. 2002, 43, 8055.
20. Ahmed, I.; Cheeseman, G. W. H.; Jaques, B. Tetrahedron 1979, 35, 1145.
21. (a) Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W. M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890.
22. (b) Cloninger, M. J.; Whitlock, H. W. J. Org. Chem. 1998, 63, 6153.
23. 3 (415.29): C, 57.84; H, 4.61; N, 6.75. Found: C, 57.61; H, 4.54; N, 6.47.