Using (+)-Carvone to access novel derivatives of (+)- ent-Cannabidiol: the first asymmetric syntheses of (+)- ent-CBDP and (+)- ent-CBDV

doi: 10.1016/j.tetlet.2021.152891. Epub 2021 Feb 5.

Alexandra E Golliher¹, Antonio J Tenorio¹, Nina O Dimauro¹, Nicolas R Mairata¹, F Omar Holguin², William Maio¹

Affiliations

PMID: 34658452
PMCID: PMC8513745 (available on 2022-03-16)
DOI: 10.1016/j.tetlet.2021.152891

Abstract

(-)-Cannabidiol [(-)-CBD] has recently gained prominence as a treatment for neuro-inflammation and other neurodegenerative disorders; interest is also developing in its synthetic enantiomer, (+)-CBD, which has a higher affinity to CB1 / CB2 receptors than the natural stereoisomer. We have developed an inexpensive, stereoselective route to access ent-CBD derivatives using (+)-carvone as a starting material. In addition to (+)-CBD, we report the first syntheses of (+)-cannabidivarin, (+)-cannabidiphorol as well as C-6 / C-8 homologues.

Keywords: Alkene Transposition, Cannabidiol (CBD), Cannabidiphorol (CBDP), Cannabidivarin (CBDV), Enantiomer Natural Products

Conflict of interest statement

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.