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

• Authors: Antal Udvardy , Attila Sipos
• Languages of publication: EN

Abstracts

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. [...]

Keywords

EN

Alkaloids; Rearrangements; Reductions; Morphinans; Aporphines

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2013
• Volume: 11
• Issue: 12
• Pages: 2022-2030

Dates

published

1 - 12 - 2013

online

26 - 9 - 2013

Contributors

author

Antal Udvardy

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

author

Attila Sipos

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

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Identifiers

DOI

10.2478/s11532-013-0330-4