Highly Stereoselective Ring Contraction of Heterocyclic Enamines: Total Synthesis of Perhydrohistrionicotoxin and Its 2,6-Epimer

Journal of Organic Chemistry

Volumn 54, Issue 18, 1989, Pages 4419-4425

  Duhamel, Pierre ^a   Kotera, Mitsuharu ^a   Monteil, Thierry ^a   Marabout, Benoit ^a   Davoust, Daniel ^b  

^a IRCOF   (France)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001756644     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00279a034     Document Type: Article

References (14)

1. Taken in the thesis of M. K. Universite de Rouen, 1987. Taken in part from the thesis of B. M. Universite de Rouen, 1988.
2. Daly, J. W. Alkaloids of Neotropical Poison Frogs (Dendroba-tide). In Progress in the Chemistry of Organic Natural Products; Hertz, W., Griesebach, H., Kirby, G. W., Eds.; Springer-Verlag: Vienna, New York, 1982; Vol. 41, pp 206–340. Takahashi, K., Jacobson, A. E.; Mak, C. P. ; Witkop, B.; Brossi, A.; Albuquerque, E. X.; Warnick, J. E.; Male-que, M. A.; Bavoso, A.; Silverton, J. V. J. Med. Chem. 1982, 25, 919. The total synthesis of (+)- and (-)-PHTX by optical resolution of a hydroxy lactam intermediate: Takahashi, K.; Witkop, B.; Brossi, A.; Maleque, M. A.; Albuquerque, E. X. Helv. Chim. Acta 1982, 65, 252.
3. The total synthesis of (±)-PHTX: (a) Corey, E. J.; Arnett, J. F.; Widiger, G. N. J. Am. Chem. Soc. 1975, 97, 430. Aratani, M.; Dunkerton, L. V.; Fukuyama, T.; Kishi, Y.; Kakoi, H.; Sugiura, S.; Inoue, S. J. Org. Chem. 1975, 40, 2009. Fukuyama, T.; Dunkerton, L. V.; Aratani, M.; Kishi, Y. J. Org. Chem. 1975, 40, 2011. Corey, E. J.; Balanson, R. D. Heterocycles 1976, 5, 445. Evans, D. A.; Thomas, E. W.; Cherpeck. R. E. J. Am. Chem. Soc. 1982. 104, 3695.
4. For reviews on synthetic studies until 1981, see: (a) Inubushi, Y.; Ibuka, T. Heterocycles 1982,17, 507. Witkop, B.; Gossinger, E. The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1983; Vol. 21, p 168. Quinkert, G.; Montforts, F. P. ; Ockenfeld, M.; Rehm, D. Synform 1984, 1.
5. Formal syntheses and aPProaches since 1982: (a) Koft, E. R.; Smith, A. B., III. J. Org. Chem. 1984, 49, 832. Glanzmann, M.; Karalai, C.; Ostersehlt, B.; Schon, U.; Frese, C.; Winterfeldt, E. Tetrahedron 1982, 38, 2805. Keck, G. E.; Yates, J. B. J. Org. Chem. 1982, 47, 3590. Godleski, S. A.; Heacock, D. J. J. Org. Chem. 1982,47, 4822. Godleski, S. A.; Heacock, D. J.; Meinhart, J. D.; Wallendael, S. V. J. Org. Chem. 1983, 48, 2101. (f) Carruthers, W.; Cumming, S. A. J. Chem. Soc., Chem. Commun. 1983, 360. (g) Carruthers, W.; Cumming, S. A. J. Chem. Soc., Perkin Trans. 1 1983, 2383. (h) Tanner, D.; Somfai, P. Tetrahedron Lett. 1985, 26, 3883. (i) Tanner, D.; Somfai, P. Tetrahedron 1986, 42, 5657. (j) Pearson, A. J.; Ham, P. J.Chem. Soc., Perkin Trans. 1 1983,1421. (k) Holmes, A. B.; Raithby, P. R.; Rosales, M. J.; Ruselle, K.; Stern, E. S.; Stubbs, M. E. Tetrahedron Lett. 1984, 25, 5705. (1) Holmes, A. B.; Ruselle, K.; Stern, E. S.; Stubbs, M. E.; Wellard, N. K. Tetrahedron Lett. 1984, 25, 4163. (m) Butlin, R. J.; Holmes, A. B.; Mcdonald, E. Tetrahedron Lett. 1988, 29, 2989. (n) Brewster, K.; Harrison, J. M.; Inch, T. D.; Williams, N. J. Chem. Soc., Perkin Trans. 1 1987, 21. (o) Winkler, J. D.; Hershberger, P. M.; SPringer, J. P. Tetrahedron Lett. 1986,27, 5177. (P) Gessner, W.; Takahashi, K.; WitkoP, B.; Brossi, A. Helv. Chim. Acta 1985, 68, 49. (q) Tanis, S. P.; Dixon, L. A. Tetrahedron Lett. 1987,28, 2495. (r) Kotera, M. Bull. Soc. Chim. Fr., in Press, (s) Daly, J. W.; SPande, T. F. Alkaloides chemical and Biological PersPectives', Pelletier, S. W., Ed.; Wiley Interscience: New York, 1986; Vol. 4. P 1–274. Winterfeldt. E. Bull. Soc. Chim. Belg. 1988. 97. 705.
6. The total synthesis of (±)-HTX: Carey, S. C.; Aratani, M.; Kishi, Y. Tetrahedron Lett. 1985. 26. 5887.
7. Duhamel, P.; Kotera, M.; Monteil, T. Bull. Chem. Soc. Jpn. 1986, 59, 2353. Duhamel, P.; Kotera, M. J. Org. Chem. 1982, 47,1688.
8. Duhamel, P.; Kotera, M. J. Chem. Res., Synop. 1982, 276; J. Chem. Res., Miniprint 1982, 2855.
9. Stevens, R. V. Acc. Chem. Res. 1984,17, 289–296. This explanation is limited by the small energy differences between chair and twist conformation observed for cycloheptene and cycloheptenone. See p 2821 in the review “Dynamic Stereochemistry of the 5-, 6- and 7-membered rings using the torsion angle notation”: Toromanoff, E. Tetrahedron 1980,36, 2809–2931.
10. Chuit, C.; Foulon, J. P.; Normant, J. F. Tetrahedron 1980, 36, 2305.
11. Tokuyama, T.; Uenoyama, K.; Brown, G.; Daly, J. W.; Witkop, B. Helv. Chim. Acta,1974, 57, 2597. Tokuyama, T.; Yamamoto, J.; Daly, J. W.; Highet, R. J. Tetrahedron 1983, 39, 49.
12. Scheibye, S.; Pedersen, B. S.; Lawesson, S. O. Bull. Soc. Chem. Beg. 1978, 87, 229.
13. Bredereck, H.; Simchen G.; Funke, B. Chem. Ber. 1971,104, 2709.
14. Mancuso, A. J.; Swern, D. Synthesis 1981, 165–185.