A new route to aristocularine alkaloids: Total synthesis of aristoyagonine

Journal of Organic Chemistry

Volumn 69, Issue 13, 2004, Pages 4527-4530

  Moreau, Anne ^a   Couture, Axel ^a   Deniau, Eric ^a   Grandclaudon, Pierre ^a  

^a UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLIZATION; PHOSPHORYLATION;

AROMATIC COMPOUNDS;

ALKALOID DERIVATIVE; ARISTOCULARINE ALKALOID DERIVATIVE; ARISTOYAGONINE; UNCLASSIFIED DRUG;

ARTICLE; OXIDATION; PHOSPHORYLATION; REACTION ANALYSIS; SYNTHESIS;

CYCLIZATION; FUMARIACEAE; ISOQUINOLINES; MOLECULAR STRUCTURE;

EID: 3042825440     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049869g     Document Type: Article

References (29)

1. Campello, M. J.; Castedo, L.; Dominguez, D.; Rodriguez de Lera, A.; Saa, J. M.; Suau, R.; Tojo, E.; Vidal, M. C. Tetrahedron Lett. 1984, 25, 5933-5936.
2. Tojo, E.; Dominguez, D.; Castedo, L. Phytochemistry 1991, 30, 1005-1010.
3. Suau, R.; Rico, R.; Lopez-Romero, J. M.; Najera, F.; Ruiz, A.; Ortiz-Lopez, F. J. Arkivoc (Zurich, Switz.) 2002, 5, 62-72.
4. Lamas, C.; Castedo, L.; Dominguez, D. Tetrahedron Lett. 1990, 31, 6247-6248.
5. de Lera, A. R.; Suau, R.; Castedo, L. J. Heterocycl. Chem. 1987, 24, 313-319.
6. Paleo, R. M.; Lamas, C.; Castedo, L.; Dominguez, D. J. Org. Chem. 1992, 57, 2029-2033.
7. Lamas, C.; Garcia, A.; Castedo, L.; Dominguez, D. Tetrahedron Lett. 1989, 30, 6927-6928.
8. Castedo, L.; Dominguez, D.; Rodriguez de Lera, A.; Tojo, E. Tetrahedron Lett. 1984, 25, 4573-4576.
9. Rodriguez de Lera, A.; Saa, J. M.; Suau, R.; Castedo, L. J. Heterocycl. Chem. 1987, 24, 613-622.
10. Garcia, A.; Castedo, L.; Dominguez, D. Tetrahedron 1995, 51, 8585-8598.
11. Suau, R.; Lopez-Romero, J. M.; Rico, R. Tetrahedron Lett. 1996, 37, 9357-9360.
12. (a) Couture, A.; Grandclaudon, P. Synthesis 1986, 576.
13. (b) Couture, A.; Grandclaudon, P.; Hooijer, S. J. Org. Chem. 1991, 56, 4977.
14. (c) Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron Lett. 1993, 34, 1479.
15. (d) Couture, A.; Deniau, E.; Grandclaudon, P.; Hoarau, C. J. Org. Chem. 1998, 63, 3128-3132.
16. (e) Lebrun, S.; Couture, A.; Deniau, E.; Grandclaudon, P. Org. Biomol. Chem. 2003, 1, 1701-1706.
17. (f) Hoarau, C.; Couture, A.; Cornet, H.; Deniau, E.; Grandclaudon, P. J. Org. Chem. 2001, 66, 8064-8069.
18. (g) Hoarau, C.; Couture, A.; Deniau, E.; Grandclaudon, P. J. Org. Chem. 2002, 67, 5846-5849.
19. (a) Horner, L.; Hoffmann, H.; Wippel, H. G. Chem. Ber. 1958, 91, 61.
20. (b) Horner, L.; Hoffmann, H.; Wippel, H. G. Chem. Ber. 1959, 92, 2499.
21. (c) Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87.
22. For a recent paper, see: Hattori, T.; Takeda, A.; Suzuki, K.; Koike, N.; Koshiishi, E.; Miyano, S. J. Chem. Soc., Perkin Trans. 1 1998, 3661-3671.
23. Clayden, J.; Menet, C. J. Tetrahedron Lett. 2003, 44, 3059-3062.
24. Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297-2360.
25. 1H NMR spectroscopy at 300 MHz and integration indicated (78 ± 5)% D at C-3 with a less extensively split signal for the benzylic proton (δ 4.87 ppm).
26. 2 (δ 4.31 ppm) and the aromatic proton at C-6′ (δ 6.47 ppm). (equation presented)
27. For example, a sizable nOe effect (10%) of the aromatic proton C-6′ (δ 7.02 ppm) was observed upon irradiation of the N-methyl group (δ 2.92) for compound 8. (equation presented)
28. (a) Xing, X.; Padmanaban, D.; Yeh, L.-A.; Cuny, G. D. Tetrahedron 2002, 58, 7903-7910.
29. (b) Marcoux, J. F.; Doyen, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10540.