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Verlagsausgabe
DOI: 10.5445/IR/1000031844
Veröffentlicht am 16.04.2018
Originalveröffentlichung
DOI: 10.3762/bjoc.8.160
Scopus
Zitationen: 3
Web of Science
Zitationen: 3

Highly enantioselective access to cannabinoid-type tricyles by organocatalytic Diels-Alder reactions

Bräse, Stefan; Volz, Nicole; Gläser, Franziska; Nieger, Martin

Abstract:
After prosperous domino reactions towards benzopyrans, the products were used as the starting material in Lewis acid catalyzed and organocatalytic Diels–Alder reactions to build up a tricyclic system. Herein, an asymmetric induction up to 96% enantiomeric excess was obtained by the use of imidazolidinone catalysts. This approach can be utilized to construct the tricyclic system in numerous natural products, in particular the scaffold of tetrahydrocannabinol (THC) being the most representative one. Compared with other published methods, condensation with a preexisting cyclohexane moiety in the precursor is needed to gain the heterogenic tricycle systems, whereas we present a novel strategy towards cannabinoid derivatives based on a flexible modular synthesis.


Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Toxikologie und Genetik (ITG)
Publikationstyp Zeitschriftenaufsatz
Jahr 2012
Sprache Englisch
Identifikator ISSN: 1860-5397
URN: urn:nbn:de:swb:90-318442
KITopen ID: 1000031844
HGF-Programm 47.02.01; LK 01
Erschienen in Beilstein journal of organic chemistry
Band 8
Seiten 1385-1392
Schlagworte Cannabinoids, Diels–Alder reaction, natural product synthesis, organocatalysis
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