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Wiley, European Journal of Organic Chemistry, 6(2009), p. 793-796, 2009

DOI: 10.1002/ejoc.200801175

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

Journal article published in 2009 by Pavel A. Donets ORCID, Jan L. Goeman, Johan Van der Eycken, Koen Robeyns, Luc Van Meervelt, Erik V. Van der Eycken
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the 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.