Short and efficient synthesis of alkylresorcinols: a route for the preparation of cannabinoids

Villano, Rosaria; Straker, Hannah E; Marzo, Vincenzo Di

doi:10.1039/d2nj03547b

Cited by 2 publications

(1 citation statement)

References 33 publications

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“…Also, Villano et al in the year 2022 condensed olivetol with commercially available Z -(+) -p -mentha-2, 8-dien-1-ol in the presence of 33 mol% of wet PTSA in toluene at 0 °C for 3 h, affording a mixture of normal (−)-CBD and Abn-CBD, which were isolated in 26% and 38% yield respectively after a chromatographic column. Importantly, under these experimental conditions, no tricyclic structure was produced [ 122 ]. A different synthetic procedure was reported by Vaillancourt et al in the year 1992 [ 123 ].…”

Section: Production Of Phytocannabinoids: From Biosynthesis To Synthe...mentioning

confidence: 99%

Synthetic Pathways to Non-Psychotropic Phytocannabinoids as Promising Molecules to Develop Novel Antibiotics: A Review

Alfei

Schito

2023

Pharmaceutics

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Due to the rapid emergence of multi drug resistant (MDR) pathogens against which current antibiotics are no longer functioning, severe infections are becoming practically untreatable. Consequently, the discovery of new classes of effective antimicrobial agents with novel mechanism of action is becoming increasingly urgent. The bioactivity of Cannabis sativa, an herbaceous plant used for millennia for medicinal and recreational purposes, is mainly due to its content in phytocannabinoids (PCs). Among the 180 PCs detected, cannabidiol (CBD), Δ8 and Δ9-tetrahydrocannabinols (Δ8-THC and Δ9-THC), cannabichromene (CBC), cannabigerol (CBG), cannabinol (CBN) and some of their acidic precursors have demonstrated from moderate to potent antibacterial effects against Gram-positive bacteria (MICs 0.5–8 µg/mL), including methicillin-resistant Staphylococcus aureus (MRSA), epidemic MRSA (EMRSA), as well as fluoroquinolone and tetracycline-resistant strains. Particularly, the non-psychotropic CBG was also capable to inhibit MRSA biofilm formation, to eradicate even mature biofilms, and to rapidly eliminate MRSA persiter cells. In this scenario, CBG, as well as other minor non-psychotropic PCs, such as CBD, and CBC could represent promising compounds for developing novel antibiotics with high therapeutic potential. Anyway, further studies are necessary, needing abundant quantities of such PCs, scarcely provided naturally by Cannabis plants. Here, after an extensive overture on cannabinoids including their reported antimicrobial effects, aiming at easing the synthetic production of the necessary amounts of CBG, CBC and CBD for further studies, we have, for the first time, systematically reviewed the synthetic pathways utilized for their synthesis, reporting both reaction schemes and experimental details.

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Section: Production Of Phytocannabinoids: From Biosynthesis To Synthe...mentioning

confidence: 99%

Synthetic Pathways to Non-Psychotropic Phytocannabinoids as Promising Molecules to Develop Novel Antibiotics: A Review

Alfei

Schito

2023

Pharmaceutics

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Rhodium-Catalyzed Asymmetric Addition to 4- or 5-Carbonyl-cycloenones through Dynamic Kinetic Resolution: Enantioselective Synthesis of (−)-Cannabidiol

Li,

Meng,

Ming

et al. 2024

Org. Lett.

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The reaction of 4/5-carbonyl-cycloalkenone 1 or its achiral isomer 1′ with organoboronic acid 2 in the presence of a chiral diene (S,S)-Fc-tfb-rhodium catalyst gave disubstituted trans-cycloalkanone 3 with high diastereo-and enantioselectivity. This highly efficient dynamic kinetic resolution is achieved by fast racemization of 1 through the formation of a dienolate followed by kinetic resolution with the chiral catalyst. The utility is demonstrated by the synthesis of key intermediates en route to (−)-cannabidiol.

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Short and efficient synthesis of alkylresorcinols: a route for the preparation of cannabinoids

Abstract: Alkylresorcinols (ARs) are phenolic lipids present in several plants and, from a synthetic point of view, are also versatile key intermediates for the production of many biologically active molecules. In...

Cited by 2 publications

References 33 publications

Synthetic Pathways to Non-Psychotropic Phytocannabinoids as Promising Molecules to Develop Novel Antibiotics: A Review

Synthetic Pathways to Non-Psychotropic Phytocannabinoids as Promising Molecules to Develop Novel Antibiotics: A Review

Rhodium-Catalyzed Asymmetric Addition to 4- or 5-Carbonyl-cycloenones through Dynamic Kinetic Resolution: Enantioselective Synthesis of (−)-Cannabidiol

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