Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Alexander Lipp
- Maximilian Selt
- Dorota Ferenc
- Dieter Schollmeyer
- Siegfried R Waldvogel
- Till Opatz
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000461843900059&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/acs.orglett.9b00419
- eISSN
- 1523-7052
- Externe Identifier
- Clarivate Analytics Document Solution ID: HP7CB
- PubMed Identifier: 30775928
- ISSN
- 1523-7060
- Ausgabe der Veröffentlichung
- 6
- Zeitschrift
- ORGANIC LETTERS
- Paginierung
- 1828 - 1831
- Datum der Veröffentlichung
- 2019
- Status
- Published
- Titel
- Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling
- Sub types
- Article
- Ausgabe der Zeitschrift
- 21
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Autoren
- Alexander Lipp
- Maximilian Selt
- Dorota Ferenc
- Dieter Schollmeyer
- Siegfried R Waldvogel
- Till Opatz
- DOI
- 10.1021/acs.orglett.9b00419
- eISSN
- 1523-7052
- ISSN
- 1523-7060
- Ausgabe der Veröffentlichung
- 6
- Zeitschrift
- Organic Letters
- Sprache
- en
- Online publication date
- 2019
- Paginierung
- 1828 - 1831
- Datum der Veröffentlichung
- 2019
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.orglett.9b00419
- Datum der Datenerfassung
- 2023
- Titel
- Total Synthesis of (−)-Oxycodone via Anodic Aryl–Aryl Coupling
- Ausgabe der Zeitschrift
- 21
Datenquelle: Crossref
- Abstract
- A fully regio- and diastereoselective electrochemical 4a-2'-coupling of a 3',4',5'-trioxygenated laudanosine derivative enables the synthesis of the corresponding morphinandienone. This key intermediate is further transformed into (-)-oxycodone through conjugate nucleophilic substitution for E-ring closure and [4 + 2] cycloaddition with photogenerated singlet oxygen to accomplish diastereoselective hydroxylation at C-14. The anodic transformation provides high yields and can be performed under constant current conditions both in a simple undivided cell or in continuous flow.
- Addresses
- Institute of Organic Chemistry , Johannes Gutenberg University Mainz , Duesbergweg 10-14 , 55128 Mainz , Germany.
- Autoren
- Alexander Lipp
- Maximilian Selt
- Dorota Ferenc
- Dieter Schollmeyer
- Siegfried R Waldvogel
- Till Opatz
- DOI
- 10.1021/acs.orglett.9b00419
- eISSN
- 1523-7052
- Externe Identifier
- PubMed Identifier: 30775928
- Funding acknowledgements
- Carl-Zeiss-Stiftung:
- Johannes Gutenberg-Universit?t Mainz:
- Open access
- false
- ISSN
- 1523-7060
- Ausgabe der Veröffentlichung
- 6
- Zeitschrift
- Organic letters
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2019
- Paginierung
- 1828 - 1831
- Datum der Veröffentlichung
- 2019
- Status
- Published
- Datum der Datenerfassung
- 2019
- Titel
- Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 21
Datenquelle: Europe PubMed Central
- Abstract
- A fully regio- and diastereoselective electrochemical 4a-2'-coupling of a 3',4',5'-trioxygenated laudanosine derivative enables the synthesis of the corresponding morphinandienone. This key intermediate is further transformed into (-)-oxycodone through conjugate nucleophilic substitution for E-ring closure and [4 + 2] cycloaddition with photogenerated singlet oxygen to accomplish diastereoselective hydroxylation at C-14. The anodic transformation provides high yields and can be performed under constant current conditions both in a simple undivided cell or in continuous flow.
- Autoren
- Alexander Lipp
- Maximilian Selt
- Dorota Ferenc
- Dieter Schollmeyer
- Siegfried R Waldvogel
- Till Opatz
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/30775928
- DOI
- 10.1021/acs.orglett.9b00419
- eISSN
- 1523-7052
- Ausgabe der Veröffentlichung
- 6
- Zeitschrift
- Org Lett
- Sprache
- eng
- Country
- United States
- Paginierung
- 1828 - 1831
- Datum der Veröffentlichung
- 2019
- Status
- Published
- Titel
- Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 21
Datenquelle: PubMed
- Beziehungen:
- Eigentum von