SYNTHESIS OF PHYTOCANNABINOIDS INCLUDING A DECARBOXYLATION STEP
method for decarboxylating a carboxylated phytocannabinoid compound of Formula I to form a phytocannabinoid compound of Formula II: Formula I Formula II wherein: R1 is selected from the group consisting of: substituted or unsubstituted C1-C5 alkyl; R2 is selected from the group consisting of: OH or O, and R3 is selected from the group consisting of: a substituted or unsubstituted cyclohexene, a substituted or unsubstituted C2-C8 alkene, or a substituted or unsubstituted C2-C8 dialkene; or R2 is O, and R2 and R3 together form a ring structure in which R2 is an internal ring atom; wherein the method includes heating a reaction mixture comprising the carboxylated phytocannabinoid compound and a polar aprotic solvent in the presence of a LiCl for a time sufficient to decarboxylate at least a portion of the carboxylated phytocannabinoid compounds and form the phytocannabinoid compound.
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Page/Page column 17
(2019/03/05)
SYNTHESIS OF PHYTOCANNABINOIDS INCLUDING A DEMETHYLATION STEP
A method for demethylating a methylated phytocannabinoid compound of Formula I to form a phytocannabinoid compound of Formula II: Formula I Formula II wherein: R1 is selected from the group consisting of: substituted or unsubstituted C1-C5 alkyl; R2 is selected from the group consisting of: OH or O, and R3 is selected from the group consisting of: a substituted or unsubstituted cyclohexene, a substituted or unsubstituted C2-C8 alkene, or a substituted or unsubstituted C2-C8 dialkene; or R2 is O, and R2 and R3 together form a ring structure in which R2 is an internal ring atom; wherein the method includes: heating a reaction mixture comprising the methylated phytocannabinoid compounds and a polar aprotic solvent in the presence of a dissolved inorganic alkaline salt for a time sufficient to demethylate at least a portion of the methylated phytocannabinoid compounds and form the phytocannabinoid compound.
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Page/Page column 17
(2019/03/05)
BIOENZYMATIC SYNTHESIS OF THC-v, CBV AND CBN AND THEIR USE AS THERAPEUTIC AGENTS
The present invention provides methods for producing cannabinoids. More specifically, the invention is directed to the bio-enzymatic synthesis of THC-v, CBV and CBN by contacting a compound according to Formula I with a cannabinoid synthase enzyme. Also described is a system for producing these pharmaceutically important cannabinoids and the use of such cannabinoids as therapeutic agents.
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(2017/10/18)
Synthetic Microbial Chemistry, XXI. Synthesis of Differanisole A, an Inducer of Differentiation
The synthesis of differanisole A (3,5-dichloro-2-hydroxy-4-methoxy-6-propylbenzoic acid, 1) was achieved in five steps from 2-pentanone.
Mori, Kenji,Kamada, Atsushi,Mori, Hideto
p. 303 - 306
(2007/10/02)
Naturally Occurring Dibenzofurans. VIII The Synthesis of Isodidymic acid
The synthesis of the lichen dibenzofuran isodidymic acid (2) (3-hydroxy-7-methoxy-9-pentyl-1-propyldibenzofuran-2-carboxylic acid) by intramolecular Ullmann coupling of methyl 3-iodo-4-(2'-iodo-5'-methoxy-3'-pentylphenoxy)-6-methoxy-2-propylbenzoate (22), and further transformations, is described.
Carvalho, Christopher F.,Sargent, Melvyn V.
p. 1765 - 1773
(2007/10/02)
Chemistry of 1,3,5-Tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene, a β-Tricarbonyl Trianion Equivalent
The title compound has been synthesized and its chemistry studied.Condensation with orthoesters, acid chlorides, or imidazolides gave aromatic compounds in a 5C + 1C condensation.A formal synthesis of lasiodiplodin has been completed.
Chan, T. H.,Stoessel, D.
p. 2423 - 2428
(2007/10/02)
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