Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization | Zendy

Paola Marzullo | Zendy; Francesca Foschi | Zendy; Davide Andrea Coppini | Zendy; Fabiola Fanchini | Zendy; Lucia Magnani | Zendy; Selina Rusconi | Zendy; Marcello Luzzani | Zendy; Daniele Passarella | Zendy

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Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization

Author(s) -

Paola Marzullo,

Francesca Foschi,

Davide Andrea Coppini,

Fabiola Fanchini,

Lucia Magnani,

Selina Rusconi,

Marcello Luzzani,

Daniele Passarella

Publication year - 2020

Publication title -

journal of natural products

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.976

H-Index - 139

eISSN - 1520-6025

pISSN - 0163-3864

DOI - 10.1021/acs.jnatprod.0c00436

Subject(s) - cannabidiol , chemistry , intramolecular force , reactivity (psychology) , stereochemistry , tetrahydrocannabinol , intramolecular reaction , cannabinoid , cannabis , medicine , psychiatry , psychology , biochemistry , alternative medicine , receptor , pathology

The chemical reactivity of cannabidiol is based on its ability to undergo intramolecular cyclization driven by the addition of a phenolic group to one of its two double bonds. The main products of this cyclization are Δ 9 -THC ( trans -Δ-9-tetrahydrocannabinol) and Δ 8 -THC ( trans -Δ-8-tetrahydrocannabinol). These two cannabinoids are isomers, and the first one is a frequently investigated psychoactive compound and pharmaceutical agent. The isomers Δ 8 - iso -THC ( trans -Δ-8- iso -tetrahydrocannabinol) and Δ 4(8) - iso -THC ( trans -Δ-4,8- iso -tetrahydrocannabinol) have been identified as additional products of intramolecular cyclization. The use of Lewis and protic acids in different solvents has been studied to investigate the possible modulation of the reactivity of CBD (cannabidiol). The complete NMR spectroscopic characterizations of the four isomers are reported. High-performance liquid chromatography analysis and 1 H NMR spectra of the reaction mixture were used to assess the percentage ratio of the compounds formed.

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