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Synthesis 2000; 2000(3): 447-451
DOI: 10.1055/s-2000-6350
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(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

Dominique Gennet* , Patrick Michel, André Rassat
  • *Ecole Normale Supérieure and CNRS, 24 rue Lhomond, 75231 Paris Cedex 05, France; Fax + 3 31 44 32 38 63; E-mail: andre.rassat@ens.fr
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Publikationsdatum:
31. Dezember 2000 (online)

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Two intermediates 9b and 9c already used by Cook and Magnus in their syntheses of indole alkaloids were obtained from the title compound 1 through a Fischer indolization procedure. Related tetracyclic intermediates 6 and 8 were also prepared: 6 having substituents at position 2 or 4 were directly obtained, while 8 with substituents at position 1 or 3 were selectively obtained through a convenient protection-deprotection scheme

bicyclic compounds - indoles - natural products - macroline/sarpagine alkaloids - Fischer indolization - heterocycles