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

Udvardy, Antal and Sipos, Attila (2013) Salutaridine and its derivatives as thebaine-equivalents in the synthesis of aporphines. CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 11 (12). pp. 2022-2030. ISSN 1895-1066

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Abstract

Here we report on 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.

Item Type: Article
Subjects: Q Science / természettudomány > QD Chemistry / kémia
SWORD Depositor: MTMT SWORD
Depositing User: MTMT SWORD
Date Deposited: 31 Mar 2014 03:01
Last Modified: 31 Dec 2014 01:15
URI: http://real.mtak.hu/id/eprint/11204

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