A Modular Formal Total Synthesis of (±)-Cycloclavine
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Natalie Netz
- Till Opatz
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000370768000043&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/acs.joc.5b02815
- Externe Identifier
- Clarivate Analytics Document Solution ID: DE6UB
- PubMed Identifier: 26811951
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- JOURNAL OF ORGANIC CHEMISTRY
- Paginierung
- 1723 - 1730
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Titel
- A Modular Formal Total Synthesis of (±)-Cycloclavine
- Sub types
- Article
- Ausgabe der Zeitschrift
- 81
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Autoren
- Natalie Netz
- Till Opatz
- DOI
- 10.1021/acs.joc.5b02815
- eISSN
- 1520-6904
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- The Journal of Organic Chemistry
- Sprache
- en
- Online publication date
- 2016
- Paginierung
- 1723 - 1730
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.joc.5b02815
- Datum der Datenerfassung
- 2023
- Titel
- A Modular Formal Total Synthesis of (±)-Cycloclavine
- Ausgabe der Zeitschrift
- 81
Datenquelle: Crossref
- Abstract
- Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence.
- Addresses
- Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
- Autoren
- Natalie Netz
- Till Opatz
- DOI
- 10.1021/acs.joc.5b02815
- eISSN
- 1520-6904
- Externe Identifier
- PubMed Identifier: 26811951
- Funding acknowledgements
- Rhineland-Palatinate Center for Natural Products Research:
- BASF:
- Open access
- false
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- The Journal of organic chemistry
- Schlüsselwörter
- Hexanes
- Indole Alkaloids
- Molecular Structure
- Alkylation
- Cyclization
- Stereoisomerism
- Bridged Bicyclo Compounds, Heterocyclic
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2016
- Paginierung
- 1723 - 1730
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Datum der Datenerfassung
- 2016
- Titel
- A Modular Formal Total Synthesis of (±)-Cycloclavine.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 81
Datenquelle: Europe PubMed Central
- Abstract
- Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence.
- Autoren
- Natalie Netz
- Till Opatz
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/26811951
- DOI
- 10.1021/acs.joc.5b02815
- eISSN
- 1520-6904
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- J Org Chem
- Schlüsselwörter
- Alkylation
- Bridged Bicyclo Compounds, Heterocyclic
- Cyclization
- Hexanes
- Indole Alkaloids
- Molecular Structure
- Stereoisomerism
- Sprache
- eng
- Country
- United States
- Paginierung
- 1723 - 1730
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2016
- Titel
- A Modular Formal Total Synthesis of (±)-Cycloclavine.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 81
Datenquelle: PubMed
- Beziehungen:
- Eigentum von