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


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.

SUBMITTER: Golliher AE 

PROVIDER: S-EPMC8513745 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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

Golliher Alexandra E AE   Tenorio Antonio J AJ   Dimauro Nina O NO   Mairata Nicolas R NR   Holguin F Omar FO   Maio William W  

Tetrahedron letters 20210205


(-)-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 <i>ent</i>-CBD derivatives using (+)-carvone as a starting material. In addition to (+)-CBD, we report the first syntheses of (+)-cannabidivarin, (+)-ca  ...[more]

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