- PROCESS FOR THE SYNTHESIS OF CANNABIDIOL AND INTERMEDIATES THEREOF
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The present invention relates to process for the preparation of cannabidiol (A) from the coupling of (D) and (E) through the intermediates (C) and (D) starting from compound (B). The invention further relates to the novel compounds (B), (C), (D) and (E) and reagents used in this process. More specifically, this invention provides the manufacturing of Cannabidiol (A) in milligram to gram or kilogram scale.
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- Monocyclic Quinone Structure-Activity Patterns: Synthesis of Catalytic Inhibitors of Topoisomerase II with Potent Antiproliferative Activity
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The monocyclic 1,4-benzoquinone, HU-331, the direct oxidation product of cannabidiol, inhibits the catalytic activity of topoisomerase II but without inducing DNA strand breaks or generating free radicals, and unlike many fused-ring quinones exhibits minimal cardiotoxicity. Thus, monocyclic quinones have potential as anticancer agents, and investigation of the structural origins of their biological activity is warranted. New syntheses of cannabidiol and (±)-HU-331 are here reported. Integrated synthetic protocols afforded a wide range of polysubstituted resorcinol derivatives; many of the corresponding novel 2-hydroxy-1,4-benzoquinone derivatives are potent inhibitors of the catalytic activity of topoisomerase II, some more so than HU-331, whose monoterpene unit replaced by a 3-cycloalkyl unit conferred increased antiproliferative properties in cell lines with IC50 values extending below 1 mM, and greater stability in solution than HU-331. The principal pharmacophore of quinones related to HU-331 was identified. Selected monocyclic quinones show potential for the development of new anticancer agents.
- Waugh, Thomas M.,Masters, John,Aliev, Abil E.,Marson, Charles M.
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supporting information
p. 114 - 124
(2019/12/11)
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- CATALYTIC CANNABINOID PROCESSES AND PRECURSORS
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The present disclosure relates to new cannabinoid sulfonate esters and processes for their use to prepare cannabinoids. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of cannabinoids from the cannabinoid sulfonate esters.
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- Process for production of delta-9- tetrahydrocannabinol
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The present invention relates to a process for preparation of a delta-9-tetrahydrocannabinol compound or derivative thereof involving treating a first intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the delta-9-tetrahydrocannabinol compound or derivative thereof. Another aspect of the present invention relates to a process for preparation of a cannabidiol or cannabidiolate compound involving reacting a first starting compound with a second starting compound in the presence of a metal triflate catalyst, under conditions effective to form the cannabidiol or cannabidiolate compound. The present invention also relates to a compound of the formula: where R8, R9, and R10 are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo, with R1, R2, and R3 defined herein.
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- BORON TRIFLUORIDE ETHERATE ON ALUMINA - A MODIFIED LEWIS ACID REAGENT. AN IMPROVED SYNTHESIS OF CANNABIDIOL.
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Boron trifluoride etherate on alumina catalyses the condensation of resorcinols and monomethyl resorcinols with several monoterpenoid allylic alcohols: in contrast to paralell reactions with boron trifluoride etherate in solution the products obtained do not undergo further cyclisations.
- Baek, Seung-Hwa,Srebnik, Morris,Mechoulam, Raphael
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p. 1083 - 1086
(2007/10/02)
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