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

Alexandra E Golliher; Antonio J Tenorio; Nina O Dimauro; Nicolas R Mairata; F Omar Holguin; William Maio

doi:10.1016/j.tetlet.2021.152891

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

Tetrahedron Lett. 2021 Mar 16:67:152891. doi: 10.1016/j.tetlet.2021.152891. Epub 2021 Feb 5.

Authors

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

Affiliations

¹ Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003.
² Department of Plant and Environmental Sciences, New Mexico State University, Las Cruces, NM 88003.

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.

Grants and funding

P20 GM103451/GM/NIGMS NIH HHS/United States