2808-33-5Relevant articles and documents
Syntheses of Amorfrutins and Derivatives via Tandem Diels-Alder and Anionic Cascade Approaches
Curtis, Brian J.,Micikas, Robert J.,Burkhardt, Russell N.,Smith, Rubin A.,Pan, Judy Y.,Jander, Katrina,Schroeder, Frank C.
, p. 11269 - 11276 (2021/04/06)
We describe two complementary approaches based on a convergent [4+2] logic toward the synthesis of amorfrutins, cannabinoids, and related plant metabolites. An anionic cascade cyclization employing β-methoxycrotonates and β-chloro-α,β-unsaturated esters yielded amorfrutins in four linear steps and demonstrated utility of β-alkoxycrotonate-derived nucleophiles as functional equivalents of β-ketoester-derived dianions. Analogously, tandem Diels-Alder/retro-Diels-Alder cycloaddition of dimedone-derived bis(trimethylsiloxy)-dienes and α,β-alkynyl ester dienophiles provided facile access to resorcinol precursors of amorfrutins and cannabinoids, avoiding late-stage installation of prenyl or geranyl moieties as in previous approaches.
PROCESS FOR THE PRODUCTION OF CANNABINOIDS AND CANNABINOID ACIDS
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Page/Page column 25, (2021/04/17)
The present invention relates to a process for the preparation of diverse known and novel cannabinoids 5, which include cannabigerol (CBG, 1), cannabigerolic acid (CBGA, 2), cannabigerovarin (CBGV, 3), cannabigerovarinic acid (CBGVA, 4) and other naturally occurring monocyclic cannabinoids and other analogues from simple inexpensive starting materials using a cascade sequence of allylic rearrangement and aromatization. Novel cannabinoids of series 5 are also claimed as part of the invention. These synthesized cannabinoids, unlike the minor cannabinoids isolated from Cannabis saliva or synthesized from the condensation reactions such as the reactions of substituted resorcinols with monoterpenes, are much easier to obtain at high purity levels. In particular, these cannabinoids, including but not limited to cannabigerol (CBG, 1), cannabigerolic acid (CBGA, 2), cannabigerovarin (CBGV, 3) and cannabigerovarinic acid (CBGVA, 4) are obtained without contamination with impurities with variation in RA and RB (e.g. contamination of CBG with CBGV).
METHODS OF SYNTHESIZING CANNABIGERGOL, CANNABIGEROLIC ACID, AND ANALOGS THEREOF
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Paragraph 00102-00110, (2021/11/20)
Disclosed are methods for preparing carmabigerol (CBG) or a CBG analog, embodiments of the method comprising providing a compound (I); combining the compound (I) with geraniol and a solvent to form a reaction mixture; and combining the reaction mixture with an acid catalyst to form a product mixture comprising CBG or the CBG analog. The method may further comprise separating the CBG or the CBG analog for the product mixture and may further comprise purifying the CBG or CBG analog. Methods for preparing cannabigerolic acid (CBGA) or a CBGA analog are also disclosed. The present disclosure also provides high purity CBG, CBGA and analogs thereof. CBG can be useful as a neuroprotectant, an antibacterial agent, etc.
