An asymmetric approach towards (-)-aphanorphine and its analogues

Donets, Pavel A.;Goeman, Jan L.;Van Der Eycken, Johan;Robeyns, Koen;Van Der Eycken, Erik V.;et.al.
(2009) European Journal of Organic Chemistry — Vol. 2009, n° 6, p. 793-796 (2009)

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Authors
  • Donets, Pavel A.
    Author
  • Goeman, Jan L.
    Author
  • Van Der Eycken, Johan
    Author
  • Robeyns, KoenUCLouvain
    Author
  • Van Der Eycken, Erik V.
    Author
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Abstract
A short enantioselective approach towards the alkaloid (-)-aphanorphine and its substituted analogues is described. The enantiomerically pure starting material for the synthesis was obtained by asymmetric hydrogenation in the presence of the Rh-(S)-PipPhos complex. Microwave-assisted Heck cyclization selectively provided the seven-membered 3-benzazepine ring. Further, the assembly of the tricyclic core of the alkaloid was accomplished by intramolecular radical cyclization. The X-ray structure confirming the absolute configuration of the obtained products is described. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
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  • KU LEUVENDepartment of Chemistry

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Donets, P. A., Goeman, J. L., Van Der Eycken, J., Robeyns, K., Van Meervelt, L., & Van Der Eycken, E. V. (2009). An asymmetric approach towards (-)-aphanorphine and its analogues. European Journal of Organic Chemistry, 2009(6), 793-796. https://doi.org/10.1002/ejoc.200801175 (Original work published 2009)