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Salutaridine and its derivatives as thebaine-equivalents in the synthesis of aporphines

  • Research Article
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Central European Journal of Chemistry

Abstract

Here we report the transformation of tetracyclic morphinan salutaridine (1) into 2,3,10,11-tetrasubstituted (R)-aporphines. This method serves as another chemical proof of the previously verified biosynthetic connection with pentacyclic morphinan-6,8-diene-type thebaine. In the presence of nucleophiles, this procedure could lead to pharmacologically interesting new tetrasubstituted aporphinoids. The enantioselective synthesis of 7S-salutaridinol (2) has been also achieved in order to investigate the acid-catalyzed reactions of this natural morphinan.

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Authors and Affiliations

  1. Department of Physical Chemistry, University of Debrecen, P.O. Box 7, H-4010, Debrecen, Hungary

    Antal Udvardy

  2. Department of Pharmaceutical Chemistry, Medical and Health Science Center, University of Debrecen, P.O. Box 70, H-4032, Debrecen, Hungary

    Attila Sipos

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  1. Antal Udvardy
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  2. Attila Sipos
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Correspondence to Attila Sipos.

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Dedicated to the memory of Professor Meinhart H. Zenk

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Udvardy, A., Sipos, A. Salutaridine and its derivatives as thebaine-equivalents in the synthesis of aporphines. cent.eur.j.chem. 11, 2022–2030 (2013). https://doi.org/10.2478/s11532-013-0330-4

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  • DOI: https://doi.org/10.2478/s11532-013-0330-4

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