A short formal synthesis of (±)-perhydrohistrionicotoxin

Synlett

Volumn , Issue 2, 2008, Pages 260-262

  Deyine, Abdallah ^a,b   Poirier, Jean Marie ^a   Duhamel, Pierre ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b INSA   (France)

Author keywords

Azaspiranic alkaloids; Hemiacetal vinylog; Michael type addition; Perhydrohistrionicotoxin; Silyl enol ether

Indexed keywords

ALDEHYDE DERIVATIVE; BORON TRIFLUORIDE; ETHER DERIVATIVE; HISTRIONICOTOXIN; PERHYDROHISTRIONICOTOXIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MICHAEL ADDITION; SYNTHESIS;

EID: 38949143242     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000877     Document Type: Article

References (36)

1. Daly, J. W.; Karle, J. L.; Myers, C. W.; Tokuyan, T.; Water, J. A.; Witkop, B. Proc Natl. Acad. Sci. U.S.A. 1971, 68, 1870.
2. (a) Gessener, W.; Takahashi, K.; Witkop, B.; Brossi, A. Helv. Chim. Acta 1985, 68, 49.
3. (b) Takahashi, K.; Jacobson, A. E.; Mak, C. P.; Witkop, B.; Brossi, A.; Albuquerque, E. X.; Warnick, J. E.; Maleque, M. A.; Bravoso, A.; Silverton, J. V. J. Med. Chem. 1982, 25, 919.
4. (c) Takahashi, K.; Witkop, B.; Brossi, A. Helv. Chim. Acta 1982, 65, 252.
5. For synthesis of perhydrohistrionicotoxin, see: (a) Kotera, M. Bull. Soc. Chim. Fr. 1989, 370.
6. (b) Stockman, R. A.; Sinclair, A.; Arini, L. G.; Szeto, P.; Hugues, D. L. J. Org. Chem. 2004, 69, 1598.
7. (c) Malassene, R.; Vanquelefe, R.; Toupet, L.; Hurvois, J.-P.; Moinet, C. Org. Biomol. Chem. 2003, 1, 547.
8. (d) McLaughlin, M. J.; Hsung, R. P.; Cole, K. P.; Hahn, J. M.; Wang, J. Org. Lett. 2002, 4, 2017.
9. (e) Kim, S.; Ko, L.; Lee, T.; Kim, D. J. Org. Chem. 2005, 70, 5756.
10. (f) Kim, D.; Shim, P. J.; Lee, J.; Park, C. W.; Hong, S. W.; Kim, S. J. Org. Chem. 2000, 65, 4864.
11. (g) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907.
12. (h) Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B. J. Org. Chem. 1989, 54, 4419.
13. (i) Duhamel, P.; Kotera, M.; Marabout, B. Tetrahedron: Asymmetry 1991, 2, 203.
14. (j) Duhamel, P.; Kotera, M.; Monteil, T. Bull. Chem. Soc. Jpn. 1986, 59, 2353.
15. (k) Pearson, A. J.; Ham, P. Tetrahedron Lett. 1980, 21, 4637.
16. (l) Pearson, A. J.; Ham, P. J. Chem. Soc., Perkin Trans. 1 1983, 1421.
17. (m) Zhu, J.; Royer, J.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1991, 32, 2485.
18. (a) Deyine, A.; Poirier, J.-M.; Duhamel, L.; Duhamel, P. Tetrahedron Lett. 2005, 46, 2491.
19. (b) Duhamel, P.; Deyine, A.; Poirier, J.-M. Tetrahedron Lett. 1993, 34, 3863.
20. (c) Duhamel, P.; Deyine, A.; Dujardin, G.; Ple, G.; Poirier, J.-M. J. Chem. Soc., Perkin Trans. 1 1995, 2103.
21. (d) Dujardin, G.; Poirier, J.-M. Bull. Soc. Chim. Fr. 1994, 900.
22. (e) Duhamel, P.; Dujardin, G.; Hennequin, L.; Poirier, J.-M. J. Chem. Soc., Perkin Trans. 1 1992, 387.
23. (f) Poirier, J.-M.; Hennequin, L. Tetrahedron 1989, 45, 4191.
24. (g) Poirier, J.-M.; Dujardin, G. Tetrahedron Lett. 1987, 28, 3337.
25. (h) Poirier, J.-M.; Hennequin, L.; Fomani, M. Bull. Soc. Chim. Fr. 1986, 436.
26. (i) Duhamel, P.; Hennequin, L.; Poirier, N.; Poirier, J.-M. Tetrahedron Lett. 1985, 26, 6201.
27. (j) Duhamel, P.; Poirier, J.-M.; Hennequin, L. Tetrahedron Lett. 1984, 25, 1471.
28. (k) Duhamel, P.; Poirier, J.-M.; Tavel, G. Tetrahedron Lett. 1984, 25, 43.
29. (l) Duhamel, P.; Hennequin, L.; Poirier, J.-M.; Tavel, G.; Vottero, C. Tetrahedron Lett. 1986, 42, 4777.
30. Garst, M. E.; Bonfiglio, J. N.; Marks, J. J. Org Chem. 1980, 45, 2307.
31. 6): δ = 153.13, 132.46, 118.78, 60.35, 43.64, 26.57, 26.29, 25.72, 24.12, 17.69, 13.31, -5.80.
32. 5b
33. 3): δ = 9.30 (s, 1 H), 4.10 (q, J = 6.7 Hz, 2 H), 4.00 (m, 2 H), 2.62 (m, 2 H), 2.20 (m, 2 H), 2.12 (s, 3 H), 1.60 (m, 6 H), 1.25 (t, J = 6.7 Hz, 3 H).
34. (a) The low yield of N-benzylation was previously reported for similar compounds.
35. (b) Holmes, A. B.; Raithby, P. R.; Russel, K.; Stern, E. S.; Stubbs, M. E.; Wellard, N. K. J. Chem. Soc., Chem. Commun. 1984, 1191.
36. 4i