Structure elucidation of hypocreolide a by enantioselective total synthesis
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Katharina Goetz
- Johannes Liermann
- Eckhard Thines
- Heidrun Anke
- Till Opatz
- Sammlungen
- metadata
- ISSN
- 1477-0520
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- Organic & biomolecular chemistry
- Schlüsselwörter
- 540 Chemie
- 540 Chemistry and allied sciences
- Sprache
- eng
- Paginierung
- Seiten: 2123 - 2130
- Datum der Veröffentlichung
- 2010
- Herausgeber
- Royal Society of Chemistry
- Herausgeber URL
- http://dx.doi.org/10.1039/c001794a
- Datum der Datenerfassung
- 2020
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2020
- Zugang
- Public
- Titel
- Structure elucidation of hypocreolide a by enantioselective total synthesis
- Ausgabe der Zeitschrift
- 8
Datenquelle: METADATA.UB
- Andere Metadatenquellen:
-
- Autoren
- Katharina Goetz
- Johannes C Liermann
- Eckhard Thines
- Heidrun Anke
- Till Opatz
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000276786000019&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1039/c001794a
- Externe Identifier
- Clarivate Analytics Document Solution ID: 584WZ
- PubMed Identifier: 20401389
- ISSN
- 1477-0520
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- ORGANIC & BIOMOLECULAR CHEMISTRY
- Paginierung
- 2123 - 2130
- Datum der Veröffentlichung
- 2010
- Status
- Published
- Titel
- Structure elucidation of hypocreolide A by enantioselective total synthesis
- Sub types
- Article
- Ausgabe der Zeitschrift
- 8
Datenquelle: Web of Science (Lite)
- Autoren
- Katharina Götz
- Johannes C Liermann
- Eckhard Thines
- Heidrun Anke
- Till Opatz
- DOI
- 10.1039/c001794a
- eISSN
- 1477-0539
- ISSN
- 1477-0520
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- Organic & Biomolecular Chemistry
- Sprache
- en
- Paginierung
- 2123 - 2123
- Datum der Veröffentlichung
- 2010
- Status
- Published
- Herausgeber
- Royal Society of Chemistry (RSC)
- Herausgeber URL
- http://dx.doi.org/10.1039/c001794a
- Datum der Datenerfassung
- 2024
- Titel
- Structure elucidation of hypocreolide A by enantioselective total synthesis
- Ausgabe der Zeitschrift
- 8
Datenquelle: Crossref
- Abstract
- The nonenolide hypocreolide A was isolated from culture filtrates of the ascomycete Hypocrea lactea. It exhibits moderate antimicrobial activity against various tested fungi and bacteria. Since neither the relative nor the absolute stereochemistry of the compound could be initially assigned, a stereochemically flexible total synthesis was developed. The two stereogenic centers were formed in high enantioselectivity and yield using transition metal catalyzed asymmetric reactions. While attempts to construct the ten-membered lactone in a ring-closing olefin metathesis gave disappointing results, a combination of cross metathesis and macrolactonization provided the title compound in nine steps and 12% overall yield.
- Addresses
- Universität Hamburg, Institut für Organische Chemie, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany.
- Autoren
- Katharina Götz
- Johannes C Liermann
- Eckhard Thines
- Heidrun Anke
- Till Opatz
- DOI
- 10.1039/c001794a
- eISSN
- 1477-0539
- Externe Identifier
- PubMed Identifier: 20401389
- Open access
- false
- ISSN
- 1477-0520
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- Organic & biomolecular chemistry
- Schlüsselwörter
- Cell Line
- Hela Cells
- Humans
- Bacteria
- Fungi
- Ascomycota
- Lactones
- Anti-Bacterial Agents
- Antifungal Agents
- Microbial Sensitivity Tests
- Drug Evaluation, Preclinical
- Cell Survival
- Molecular Structure
- Structure-Activity Relationship
- Stereoisomerism
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2010
- Paginierung
- 2123 - 2130
- Datum der Veröffentlichung
- 2010
- Status
- Published
- Datum der Datenerfassung
- 2010
- Titel
- Structure elucidation of hypocreolide A by enantioselective total synthesis.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 8
Datenquelle: Europe PubMed Central
- Abstract
- The nonenolide hypocreolide A was isolated from culture filtrates of the ascomycete Hypocrea lactea. It exhibits moderate antimicrobial activity against various tested fungi and bacteria. Since neither the relative nor the absolute stereochemistry of the compound could be initially assigned, a stereochemically flexible total synthesis was developed. The two stereogenic centers were formed in high enantioselectivity and yield using transition metal catalyzed asymmetric reactions. While attempts to construct the ten-membered lactone in a ring-closing olefin metathesis gave disappointing results, a combination of cross metathesis and macrolactonization provided the title compound in nine steps and 12% overall yield.
- Autoren
- Katharina Götz
- Johannes C Liermann
- Eckhard Thines
- Heidrun Anke
- Till Opatz
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/20401389
- DOI
- 10.1039/c001794a
- eISSN
- 1477-0539
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- Org Biomol Chem
- Schlüsselwörter
- Anti-Bacterial Agents
- Antifungal Agents
- Ascomycota
- Bacteria
- Cell Line
- Cell Survival
- Drug Evaluation, Preclinical
- Fungi
- HeLa Cells
- Humans
- Lactones
- Microbial Sensitivity Tests
- Molecular Structure
- Stereoisomerism
- Structure-Activity Relationship
- Sprache
- eng
- Country
- England
- Paginierung
- 2123 - 2130
- Datum der Veröffentlichung
- 2010
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2010
- Titel
- Structure elucidation of hypocreolide A by enantioselective total synthesis.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 8
Datenquelle: PubMed
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- Eigentum von