Bitte benutzen Sie diese Kennung, um auf die Ressource zu verweisen:
http://dx.doi.org/10.18419/opus-13578
Autor(en): | Greb, Julian Drennhaus, Till Klischan, Moritz K. T. Schroeder, Zachary W. Frey, Wolfgang Pietruszka, Jörg |
Titel: | A common C2‐symmetric 2,2’‐biphenol building block and its application in the synthesis of (+)‐di‐epi‐gonytolide A |
Erscheinungsdatum: | 2023 |
Dokumentart: | Zeitschriftenartikel |
Seiten: | 9 |
Erschienen in: | Chemistry - a european journal 29 (2023), No. e202300941 |
URI: | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-ds-135973 http://elib.uni-stuttgart.de/handle/11682/13597 http://dx.doi.org/10.18419/opus-13578 |
ISSN: | 0947-6539 1521-3765 |
Zusammenfassung: | A variety of biaryl polyketides exhibit remarkable bioactivities. However, their synthetic accessibility is often challenging. Herein, the enantioselective preparation and synthetic application of an axially chiral 2,2’‐biphenol building block is outlined that represents a common motif of these intriguing natural products. Based on the highly regioselective and scalable bromination of a phenol precursor, a coupling process by Lipshutz cuprate oxidation was developed. A copper‐mediated deracemization strategy proved to be superior to derivatization or kinetic resolution approaches. Key steps in the overall building block synthesis were rationalized through DFT studies. Utilizing the 2,2’‐biphenol, a highly diastereoselective five step synthesis of formerly unknown (+)‐di‐epi‐gonytolide A was developed, thus showcasing the building block's general potential for the synthesis of natural products and their derivatives. En route, the first enantioselective construction of a chromone dimer intermediate was established. |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
---|---|---|---|---|
CHEM_CHEM202300941.pdf | 7,91 MB | Adobe PDF | Öffnen/Anzeigen |
Diese Ressource wurde unter folgender Copyright-Bestimmung veröffentlicht: Lizenz von Creative Commons