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Solid-Phase Synthesis of Anandamide Analogues

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journal contribution
posted on 13.05.2004, 00:00 by Longwu Qi, Michael M. Meijler, Sang-Hyeup Lee, Chengzao Sun, Kim D. Janda
The endocannabinoids are amides and esters of arachidonic acid that can mimic the pharmacological properties of Δ9-tetrahydrocannabinol (Δ9-THC). Anandamide, the most prominent of the endocannabinoids, has been implicated in both metabolic/physiological roles of the central nervous system, making it an attractive medicinal target. As such, we report the first solid-phase methodology that expedites access to various anandamide analogues. Our synthesis features a repetitive Cu-mediated coupling reaction between terminal alkynes and propargyl halides or allylic halides.