(endo, endo)-9-Benzyl-9-azabicyclo[3.3.1]nonane-2,6-diol: An intermediate for the preparation of indole alkaloids of the macroline/sarpagine series

Synthesis

Volumn , Issue 3, 2000, Pages 447-451

  Gennet, Dominique ^a   Michel, Patrick ^a   Rassat, André ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Bicyclic compounds; Fischer indolization; Heterocycles; Indoles; Macroline sarpagine alkaloids; Natural products

Indexed keywords

ALKALOID DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034091818     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6350     Document Type: Article

References (17)

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2. (b) Hamaker, L. K.; Cook, J. M. The Synthesis of Macroline Related Alkaloids; In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press: London, 1995, Vol. 9; p 23.
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8. Michel, P.; Rassat, A., submitted to J. Org. Chem.
9. N-benzyl could also be used instead of N-benzoyl 4 in the indole syntheses, but the yield were not as good, ca 65% compared to ca 95% with 4.
10. It is necessary to liberate the alcohol function at this stage, because when the protected alcohol was used in the indolization reactions, the expected formation of an indole derivative was not observed by NMR.
11. Ishii, H. Acc. Chem. Res. 1981, 14, 275.
12. (a) Szczepankiewicz, B. G.; Heathcock, C. H. Tetrahedron 1997, 53, 8853.
13. (b) Murakami, Y.; Watanabe, T.; Takahashi, H.; Yokoo, H.; Nakazawa, Y.; Koshimizu, M.; Adachi, N.; Kurita, M.; Yoshino, T.; Inagaki, T.; Ohishi, M.; Watanabe, M.; Tani, M.; Yokoyama, Y. Tetrahedron 1998, 54, 45.
14. For a example of hydrogenolysis of a bromoindole, see: Tsuji, S.; Rinehart, K. L.; Gunasekera, S. P.; Kashman, Y.; Cross, S. S.; Lui, M. S.; Pomponi, S. A.; Diaz, M. C. J. Org. Chem. 1988, 53, 5446.
15. Michel, P., Thèse de Doctorat 1999, Université Pierre et Marie Curie, Paris.
16. b-benzyl derivatives simplified the NMR spectra.
17. Mashimo, K.; Sato, Y. Tetrahedron 1970, 26, 803.