A Meisenheimer rearrangement approach to bridgehead hydroxylated tropane alkaloid derivatives

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 97-100

  Bremner, John B ^b   Smith, Reginald J ^a   Tarrant, Gregory J ^b  

^a Phytex Australia Pty Ltd   (Australia)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

TROPANE ALKALOID;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030062956     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02082-9     Document Type: Article

References (20)

1. Ducrot, P.-H.; Lallemand, J. Y. Tetrahedron Lett. 1990, 27, 3879.
2. Goldmann, A.; Milat, M.-L., Ducrot, P.-H.; Lallemand, J. Y.; Maille, M.; Lepingle, A.; Charpin, I.; Tepfer, D. Phytochemistry 1990, 29, 2125.
3. Asano, N.; Tomioka, E.; Kizu, H.; Matsui, K. Carbohydr. Res. 1994, 253, 235.
4. Molyneux, R. J.; Pan, Y. T.; Goldmann, A.; Tepfer, D. A.; Elbein, A. D. Arch.Biochem.Biophys. 1993, 304, 81.
5. Ray, A. B.; Oshima Y.; Hikino H.; Kabuto C. Heterocycles 1982, 19, 1233.
6. Pinder, A. R. J. Org. Chem. 1982, 47, 3607.
7. Justice, D. E.; Malpass, J. R. J. Chem. Soc. Perkin Trans. 1 1994, 2559.
8. Hayakawa, Y.; Baba, Y.; Makino, S.; Noyori, R. J. Am. Chem. Soc. 1978, 100, 1786.
9. Fodor, G. in "Chemistry of the Alkaloids" (Pelletier, S. W. Ed) (p 448), Van Nostrand Reinhold, New York, 1970.
10. All new compounds gave spectral data consistent with the proposed structures.
11. 3 at 400MHz.
12. Glaser, R. Magn. Reson. Chem. 1993, 31, 335, and reference therein.
13. 13C).
14. Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818.
15. Naylor, A.; Howarth, N.; Malpass, J. R. Tetrahedron 1993, 49, 451.
16. th Ed) (pp 1018-1019), Wiley-Interscience, New York, 1992, and references therein.
17. -1.
18. -1.
19. -1.
20. -1.