Synthesis of Neocannabinoids Using Controlled Friedel-Crafts Reactions

Millimaci, Alexandra; Trilles, Richard; McNeely, James; Brown, Lauren E.; Beeler, Aaron B.; Porco, John A.

doi:10.26434/chemrxiv-2023-7wtzg

Cited by 2 publications

(2 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Friedel–Crafts method relies on electrophilic aromatic substitution reactions, where desired cannabinoids are formed through the reaction of aromatic compounds with electrophiles. All these methods require quality control, analysis, and specialized knowledge to ensure the purity and compliance of the obtained cannabinoids with specific standards [ 7 , 8 , 9 ].…”

Section: Methods Of Obtaining Cannabinoidsmentioning

confidence: 99%

Therapeutic Potential of Minor Cannabinoids in Dermatological Diseases—A Synthetic Review

Kwiecień,

Kowalczuk

2023

Molecules

View full text Add to dashboard Cite

Dermatological diseases pose a significant burden on the quality of life of individuals and can be challenging to treat effectively. In this aspect, cannabinoids are gaining increasing importance due to their therapeutic potential in various disease entities including skin diseases. In this synthetic review, we comprehensively analyzed the existing literature in the field of potential dermatological applications of a lesser-known subgroup of cannabinoids, the so-called minor cannabinoids, such as cannabidivarin (CBDV), cannabidiforol (CBDP), cannabichromene (CBC), tetrahydrocannabivarin (THCV), cannabigerolic acid (CBGA), cannabigerol (CBG), cannabielsoin (CBE), cannabimovone (CBM) or cannabinol (CBN), while drawing attention to their unique pharmacological properties. We systematically searched the available databases for relevant studies and analyzed the data to provide an overview of current thematic knowledge. We looked through the full-text, bibliographic and factographic databases, especially Scopus, Web of Science, PubMed, Polish Scientific Journals Database, and selected the most relevant papers. Our review highlights that minor cannabinoids exhibit diverse pharmacological activities, including anti-inflammatory, analgesic, antimicrobial, and anti-itch properties. Several studies have reported their efficacy in mitigating symptoms associated with dermatological diseases such as psoriasis, eczema, acne, and pruritus. Furthermore, minor cannabinoids have shown potential in regulating sebum production, a crucial factor in acne pathogenesis. The findings of this review suggest that minor cannabinoids hold therapeutic promise in the management of dermatological diseases. Further preclinical and clinical investigations are warranted to elucidate their mechanisms of action, determine optimal dosage regimens, and assess long-term safety profiles. Incorporating minor cannabinoids into dermatological therapies could potentially offer novel treatment options of patients and improve their overall well-being.

show abstract

Section: Methods Of Obtaining Cannabinoidsmentioning

confidence: 99%

Therapeutic Potential of Minor Cannabinoids in Dermatological Diseases—A Synthetic Review

Kwiecień,

Kowalczuk

2023

Molecules

View full text Add to dashboard Cite

show abstract

“…are inventors on a provisional patent application describing the synthesis of neocannabinoid isomers. A version of this manuscript was deposited on the preprint repository ChemRxiv …”

mentioning

confidence: 99%

Synthesis of Neocannabinoids Using Controlled Friedel–Crafts Reactions

Millimaci,

Trilles,

McNeely

et al. 2023

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

A one-step transformation to produce 8,9-dihydrocannabidiol (H 2 CBD) and related "neocannabinoids" via controlled Friedel−Crafts reactions is reported. Experimental and computational studies probing the mechanism of neocannabinoid synthesis from cyclic allylic alcohol and substituted resorcinol reaction partners provide understanding of the kinetic and thermodynamic factors driving regioselectivity for the reaction. Herein, we present the reaction scope for neocannabinoid synthesis including the production of both normal and abnormal isomers under both kinetic and thermodynamic control. Discovery and optimization of this onestep protocol between various allylic alcohols and resorcinol derivatives are discussed and supported with density functional theory calculations.

show abstract

Synthesis of Neocannabinoids Using Controlled Friedel-Crafts Reactions

Cited by 2 publications

References 33 publications

Therapeutic Potential of Minor Cannabinoids in Dermatological Diseases—A Synthetic Review

Therapeutic Potential of Minor Cannabinoids in Dermatological Diseases—A Synthetic Review

Synthesis of Neocannabinoids Using Controlled Friedel–Crafts Reactions

Contact Info

Product

Resources

About