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  1. 1 2013

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  1. 1 Sipos A.

  2. 1 Udvardy A.

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

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Udvardy A., Sipos A.
Open Chemistry
|
2013
|
vol. 11
|
issue 12
2022-2030
EN
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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