Synthesis of Functionalized Cannabilactones

A new approach to synthesize cannabilactones using Suzuki cross-coupling reaction followed by one-step demethylation-cyclization is presented. The two key cannabilactone prototypes AM1710 and AM1714 were obtained selectively in high overall yields and in a lesser number of synthetic steps when compa...

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Published inMolecules (Basel, Switzerland) Vol. 25; no. 3; p. 684
Main Authors Liu, Yingpeng, Ho, Thanh C, Baradwan, Mohammed, Pascual Lopez-Alberca, Maria, Iliopoulos-Tsoutsouvas, Christos, Nikas, Spyros P, Makriyannis, Alexandros
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 06.02.2020
MDPI
Subjects
Acids
cannabilactones
cannabinoids
Cannabinoids - chemical synthesis
cb2 selective ligands
Chemical reactions
Chromones - chemical synthesis
Cross coupling
Demethylation
Pain
Prototypes
suzuki cross-coupling
Tetrahydrocannabinol
THC
cannabilactones
cannabinoids
CB2 selective ligands
Suzuki cross-coupling
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Summary:A new approach to synthesize cannabilactones using Suzuki cross-coupling reaction followed by one-step demethylation-cyclization is presented. The two key cannabilactone prototypes AM1710 and AM1714 were obtained selectively in high overall yields and in a lesser number of synthetic steps when compared to our earlier synthesis. The new approach expedited the synthesis of cannabilactone analogs with structural modifications at the four potential pharmacophoric regions.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25030684