10.1021/ol060692h
The research focuses on developing a method to synthesize cannabidiol (CBD) and its analogues. The study highlights the potential of CBD as a nonpsychotropic drug due to its lack of binding to receptors responsible for psychoactivity, unlike ?9-tetrahydrocannabinol (?9-THC). The key reaction involves nickel-catalyzed allylation of 2-cyclohexene-1,4-diol monoacetate using a new reagent system, (alkenyl)ZnCl/TMEDA, achieving 94% regioselectivity and good yield. This method allows for the synthesis of CBD and its analogues, including those with longer alkenyl side chains. The research also explores the synthesis of metabolites like 7-hydroxy-CBD and demonstrates the transformation of synthesized compounds into CBD and ?9-THC. Chemicals such as lithium isopropenyl borate, alkenyl Grignard reagents, and various metal catalysts (e.g., NiCl2(tpp)2) play crucial roles in achieving the desired products with high regioselectivity and yield.
10.1016/j.tet.2007.06.006
The research aims to develop an efficient and concise method for synthesizing metabolites of tetrahydrocannabinols (THC) and tetrahydrocannabivarin (THCV), including their deuterated forms, which are crucial for analyzing biological and toxicological samples. The study introduces a streamlined synthetic approach using commercially available starting materials, such as (+)-(1R)-nopinone, to obtain key intermediates in just four steps. The methodology employs an optimized Shapiro reaction and avoids undesirable oxidative conditions, resulting in significantly improved overall yields and high optical purity. The researchers successfully synthesized eight regiospecifically deuterated metabolites without deuterium scrambling or loss, demonstrating the method's efficiency and applicability for preparative-scale production. This work provides a valuable tool for future studies on the biological and toxicological effects of these compounds.
10.1016/j.bmc.2007.08.039
The research focuses on the exploration of structural similarities between anandamide (AEA) and Δ9-tetrahydrocannabinol (Δ9-THC) by designing and synthesizing hybrid structures. The purpose of this study was to broaden the understanding of these structural similarities and to develop novel THC/AEA hybrid ligands with potential novel pharmacological properties. The researchers synthesized a series of hybrid compounds, among which Hybrid 1 (O-2220) demonstrated very high binding affinity to CB1 receptors. The study concluded that the high receptor affinity and pharmacological potency of O-2220 provide further insights into the structural requirements for biological activity shared by THC and AEA, and that the hybrids developed in this study show potential for developing new templates for cannabinoid receptor agonists and antagonists. The chemicals used in the process included various organic compounds such as anandamide, Δ9-THC, and their analogs, as well as reagents like ethanol, emulphor, and saline for drug preparation and administration. Additionally, a range of synthetic intermediates and final hybrid compounds were prepared using a variety of chemical reactions and techniques, as detailed in the chemistry section of the article.
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