A short and efficient synthesis of bridgehead mono-and dideuteriated tropinones

European Journal of Organic Chemistry

Volumn , Issue 1, 2010, Pages 152-156

  Fournial, Anaïs ^a   Ranaivondrambola, Tsiresy ^a   Mathé Allainmat, Monique ^a   Robins, Richard J ^a   Lebreton, Jacques ^a  

^a UNIVERSITÉ DE NANTES   (France)

Author keywords

Alkaloids; Deuterium; Isotopic labeling; Tropane

Indexed keywords

EID: 73349097836     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901018     Document Type: Article

References (38)

1. M. Lounasmaa, T. Tamminen, The tropane alkaloids, in: The Alkaloids (Ed.: A. Brossi), Academic Press, New York, 1993, vol. 44, p. 1.
2. a) V. Chagnault, P. Compain, K. Lewinski, K. Ikeda, N. Asano, O. R. Martin, J. Org. Chem. 2009, 74, 3179;
3. R. N. Monrad, C. B. Pipper, R. Madsen, Eur. J. Org. Chem. 2009, 3387, and references cited therein.
4. a) B. Dräger, Nat. Prod. Rep. 2004, 21, 211;
5. E. Eich, Solanaceae and Convolvulaceae: Secondary Metabolites, Springer, Berlin, 2008.
6. T. Hashimoto, Y. Yamada, Plant Physiol. 1986, 81, 619.
7. P. Pellinen, P. Honkakoski, F. Stenback, M. Niemitz, E. Alhava, O. Pelkonen, M. Lang, M. Pasanen, Eur. J. Pharmacol. 1994, 270, 35.
8. a) M. T. Long, D. J. Hopper, P. W. Trudgill, FEMS Microbiol. Lett. 1993, 106, 111;
9. B. A. Bartholomew, M. J. Smith, P. W. Trudgill, D. J. Hopper, Appl. Environ. Microbiol. 1996, 62, 3245.
10. a) E. C. Blossey, H. Budzikiewicz, M. Ohashi, G. Fodor, C. Djerassi, Tetrahedron 1964, 20, 585;
11. D. Gagnaire, P. Vottero, Bull. Soc. Chim. Fr. 1970, 164;
12. M. Majewski, G.-Z. Zheng, Can. J. Chem. 1992, 70, 2618.
13. For recent examples, see: a) S. J. Haycock-Lewandowski, A. Wilder, J. Åhman, Org. Process Res. Dev. 2008, 12, 1094;
14. N. M. Paul, M. Taylor, R. Kumar, J. R. Deschamps, R. R. Luedtke, A. Hauck Newman, J. Med. Chem. 2008, 51, 6095.
15. R. Willstätter, Justus Liebigs Ann. Chem. 1903, 317, 204.
16. R. Robinson, J. Chem. Soc. 1917, 762.
17. J. E. Burks, L. Espinosa, E. S. LaBell, J. M. McGill, A. R. Ritter, J. L. Speakman, M.-A. Williams, Org. Process Res. Dev. 1997, 1, 198.
18. a) T. L. MacDonald, R. Dolan, J. Org. Chem. 1979, 44, 4973;
19. H. O. Krabbenhoft, J. Org. Chem. 1979, 44, 4285.
20. a) Y. Hayakawa, Y. Baba, S. Makino, R. Noyori, J. Am. Chem. Soc. 1978, 100, 1786;
21. N. Cramer, S. Laschat, A. Baro, Organometallics 2006, 25, 2284, and references cited therein.
22. K. Mikami, H. Ohmura, Chem. Commun. 2002, 2626.
23. T. Shono, Y. Matsumura, K. Uchida, H. Kobayashi, J. Org. Chem. 1985, 50, 3243.
24. a) B. S. Gourlay, P. P. Molesworth, J. H. Ryan, J. A. Smith, Tetrahedron Lett. 2006, 47, 799;
25. A. R. Ekkati, D. K. Bates, Synthesis 2003, 1959.
26. a) T. Iwasaki, T. Nishitani, H. Horikawa, I. Inoue, J. Org. Chem. 1982, 47, 3799;
27. For a recent example, see: S. Nad, S. Roller, R. Haag, R. Breinbauer, Org. Lett. 2006, 8, 403.
28. T. H. Jones, R. J. Highet, A. W. Don, M. S. Blum, J. Org. Chem. 1986, 51, 2712.
29. S. Balasubramaniam, I. S. Aidhen, Synthesis 2008, 3707.
30. B.p. 102 °C (2mmHg) for the non-deuteriated compound; see: J. Fakstorp, D. Raleigh, L. E. Schniepp, J. Am. Chem. Soc. 1950, 72, 869;
31. b.p. 144-146 °C for 2, 5-dimethoxytetrahydrofuran (8).
32. M. Harding, R. Hodgson, A. Nelson, J. Chem. Soc. Perkin Trans. 1 2002, 2403.
33. The hydrolysis of 2, 5-dibutoxytetrahydrofuran (10) was completed after 2 h at 100 °C instead of 30 min at 95 °C with 2, 5-dimethoxytetrahydrofuran (6).
34. 1H] ratio more accurately (see the Supporting Information).
35. Note that direct treatment of the crude aldehyde in nBuOH in the presence of APTS to yield the corresponding acetal is less efficient.
36. This protected aldehyde 13 was found to be rather unstable, particularly during purification on silica, even in the presence of triethylamine.
37. Y. Hayakawa, R. Noyori, Bull. Chem. Soc. Jpn. 1974, 47, 2617.
38. R. J. Robins, P. Bachmann, J. G. Woolley, J. Chem. Soc. Perkin Trans. 1 1994, 615.