- Titel
- Brønsted Acid Catalyzed Asymmetric Synthesis of cis-Tetrahydrocannabinoids
- Zitierfähige Url:
- https://nbn-resolving.org/urn:nbn:de:bsz:15-qucosa2-995143
- Quellenangabe
- Angewandte Chemie International Edition
Erscheinungsjahr: 2023
Jahrgang: 62
Heft: 24
ISSN: 1433-7851
E-ISSN: 1521-3773
Artikelnummer: e202302475 - Erstveröffentlichung
- 2023
- Abstract (EN)
- We report herein the catalytic asymmetric cyclization of 1-aryl terpenols to afford enantiomerically highly enriched Δ9-cis-tetrahydrocannabinoid scaffolds in a single step. As powerful chiral catalysts strongly acidic imidodiphosphorimidates (IDPis) have been identified which furnish the products with good yields and excellent enantioselectivity. Upon MOM-deprotection some naturally occurring cannabimimetica such as (−)-cis-Δ9-tetrahydrocannabinol and (−)-perrottetinene as well as some unnatural analogues were made accessible along a merely 3-step biomimetic sequence (MOM=methoxymethyl).
- Andere Ausgabe
- Erstveröffentlichung
DOI: 10.1002/anie.202302475 - Freie Schlagwörter (EN)
- Asymmetric Synthesis, Biomimetic Synthesis, Natural Products, Organocatalysis, Oxygen Heterocycles
- Klassifikation (DDC)
- 540
- Verlag
- Wiley-VCH, Weinheim
- Förder- / Projektangaben
- Deutsche Forschungsgemeinschaft (DFG)
ID: SCHN 441/11-2 - Version / Begutachtungsstatus
- publizierte Version / Verlagsversion
- URN Qucosa
- urn:nbn:de:bsz:15-qucosa2-995143
- Veröffentlichungsdatum Qucosa
- 07.10.2025
- Dokumenttyp
- Artikel
- Sprache des Dokumentes
- Englisch
- Lizenz / Rechtehinweis
CC BY-NC-ND 4.0