Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Clemes Dialer
- Dennis Imbri
- Steven Peter Hansen
- Till Opatz
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000365462600044&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/acs.joc.5b02194
- Externe Identifier
- Clarivate Analytics Document Solution ID: CX1NJ
- PubMed Identifier: 26473557
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 22
- Zeitschrift
- JOURNAL OF ORGANIC CHEMISTRY
- Paginierung
- 11605 - 11610
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Titel
- Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization
- Sub types
- Article
- Ausgabe der Zeitschrift
- 80
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Autoren
- Clemes Dialer
- Dennis Imbri
- Steven Peter Hansen
- Till Opatz
- DOI
- 10.1021/acs.joc.5b02194
- eISSN
- 1520-6904
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 22
- Zeitschrift
- The Journal of Organic Chemistry
- Sprache
- en
- Online publication date
- 2015
- Paginierung
- 11605 - 11610
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.joc.5b02194
- Datum der Datenerfassung
- 2023
- Titel
- Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization
- Ausgabe der Zeitschrift
- 80
Datenquelle: Crossref
- Abstract
- An electrocyclic ring closure of a 2-azapentadienyl anion generated in situ from a chalcone and glycine ester is the key step of an efficient synthesis of the pyrrole core of the lamellarin alkaloids. A recently developed scalable one-pot procedure provides multigram quantities of a 3,5-diaryl-4-iodopyrrole-2-carboxylate intermediate which is transformed in four further high-yielding operations including a one-pot Pomeranz-Fritsch alkylation/cyclization and an Ullmann-type lactone ring closure into the pentacyclic lamellarin skeleton.
- Addresses
- Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
- Autoren
- Clemes Dialer
- Dennis Imbri
- Steven Peter Hansen
- Till Opatz
- DOI
- 10.1021/acs.joc.5b02194
- eISSN
- 1520-6904
- Externe Identifier
- PubMed Identifier: 26473557
- Funding acknowledgements
- Carl-Zeiss-Stiftung:
- Open access
- false
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 22
- Zeitschrift
- The Journal of organic chemistry
- Schlüsselwörter
- Anions
- Ethers
- Pyrroles
- Coumarins
- Isoquinolines
- Molecular Structure
- Alkylation
- Cyclization
- Stereoisomerism
- Heterocyclic Compounds, 4 or More Rings
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2015
- Paginierung
- 11605 - 11610
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Datum der Datenerfassung
- 2015
- Titel
- Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 80
Datenquelle: Europe PubMed Central
- Abstract
- An electrocyclic ring closure of a 2-azapentadienyl anion generated in situ from a chalcone and glycine ester is the key step of an efficient synthesis of the pyrrole core of the lamellarin alkaloids. A recently developed scalable one-pot procedure provides multigram quantities of a 3,5-diaryl-4-iodopyrrole-2-carboxylate intermediate which is transformed in four further high-yielding operations including a one-pot Pomeranz-Fritsch alkylation/cyclization and an Ullmann-type lactone ring closure into the pentacyclic lamellarin skeleton.
- Autoren
- Clemes Dialer
- Dennis Imbri
- Steven Peter Hansen
- Till Opatz
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/26473557
- DOI
- 10.1021/acs.joc.5b02194
- eISSN
- 1520-6904
- Ausgabe der Veröffentlichung
- 22
- Zeitschrift
- J Org Chem
- Schlüsselwörter
- Alkylation
- Anions
- Coumarins
- Cyclization
- Ethers
- Heterocyclic Compounds, 4 or More Rings
- Isoquinolines
- Molecular Structure
- Pyrroles
- Stereoisomerism
- Sprache
- eng
- Country
- United States
- Paginierung
- 11605 - 11610
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2016
- Titel
- Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 80
Datenquelle: PubMed
- Beziehungen:
- Eigentum von