Total Synthesis of (-)-Hymenosetin
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Ulrich Kauhl
- Lars Andernach
- Stefan Weck
- Louis P Sandjo
- Stefan Jacob
- Eckhard Thines
- Till Opatz
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000367701900023&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/acs.joc.5b02526
- Externe Identifier
- Clarivate Analytics Document Solution ID: DA3MN
- PubMed Identifier: 26636831
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 1
- Zeitschrift
- JOURNAL OF ORGANIC CHEMISTRY
- Paginierung
- 215 - 228
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Titel
- Total Synthesis of (-)-Hymenosetin
- Sub types
- Article
- Ausgabe der Zeitschrift
- 81
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Autoren
- Ulrich Kauhl
- Lars Andernach
- Stefan Weck
- Louis P Sandjo
- Stefan Jacob
- Eckhard Thines
- Till Opatz
- DOI
- 10.1021/acs.joc.5b02526
- eISSN
- 1520-6904
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 1
- Zeitschrift
- The Journal of Organic Chemistry
- Sprache
- en
- Online publication date
- 2015
- Paginierung
- 215 - 228
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.joc.5b02526
- Datum der Datenerfassung
- 2023
- Titel
- Total Synthesis of (−)-Hymenosetin
- Ausgabe der Zeitschrift
- 81
Datenquelle: Crossref
- Abstract
- The 3-decalinoyltetramic acid (-)-hymenosetin and its N-methyl analogue were prepared in 11 and 8 steps, respectively, from (+)-citronellal using an intramolecular Diels-Alder reaction as the key step. This method represents the first example for the synthesis of a 3-decalinoyltetramic acid with a free NH moiety. The stereochemistry of the title compound, an unnatural diastereomer, and of a decalin building block was studied in detail using circular dichroism spectroscopy in the IR and UV/VIS freqeuncy range. This allowed to determine the absolute configuration of the natural product and to plan the synthetic route.
- Addresses
- Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
- Autoren
- Ulrich Kauhl
- Lars Andernach
- Stefan Weck
- Louis P Sandjo
- Stefan Jacob
- Eckhard Thines
- Till Opatz
- DOI
- 10.1021/acs.joc.5b02526
- eISSN
- 1520-6904
- Externe Identifier
- PubMed Identifier: 26636831
- Funding acknowledgements
- BASF:
- Rhineland-Palatinate Center for Natural Product Research:
- Open access
- false
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 1
- Zeitschrift
- The Journal of organic chemistry
- Schlüsselwörter
- Pyrrolidinones
- Biological Products
- Molecular Structure
- Stereoisomerism
- Cycloaddition Reaction
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2015
- Paginierung
- 215 - 228
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Datum der Datenerfassung
- 2015
- Titel
- Total Synthesis of (-)-Hymenosetin.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 81
Datenquelle: Europe PubMed Central
- Abstract
- The 3-decalinoyltetramic acid (-)-hymenosetin and its N-methyl analogue were prepared in 11 and 8 steps, respectively, from (+)-citronellal using an intramolecular Diels-Alder reaction as the key step. This method represents the first example for the synthesis of a 3-decalinoyltetramic acid with a free NH moiety. The stereochemistry of the title compound, an unnatural diastereomer, and of a decalin building block was studied in detail using circular dichroism spectroscopy in the IR and UV/VIS freqeuncy range. This allowed to determine the absolute configuration of the natural product and to plan the synthetic route.
- Autoren
- Ulrich Kauhl
- Lars Andernach
- Stefan Weck
- Louis P Sandjo
- Stefan Jacob
- Eckhard Thines
- Till Opatz
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/26636831
- DOI
- 10.1021/acs.joc.5b02526
- eISSN
- 1520-6904
- Ausgabe der Veröffentlichung
- 1
- Zeitschrift
- J Org Chem
- Schlüsselwörter
- Biological Products
- Cycloaddition Reaction
- Molecular Structure
- Pyrrolidinones
- Stereoisomerism
- Sprache
- eng
- Country
- United States
- Paginierung
- 215 - 228
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2016
- Titel
- Total Synthesis of (-)-Hymenosetin.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 81
Datenquelle: PubMed
- Beziehungen:
- Eigentum von