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The Diels-Alder Approach towards Cannabinoid Derivatives and Formal Synthesis of Tetrahydrocannabinol (THC).

ABSTRACT: Based on the Diels-Alder reaction of vinylchromenes with electron-poor dienophiles, we developed a strategy for the synthesis of tetrahydrocannabinol derivatives. Substituted vinyl chromenes could be converted with several dienophiles to successfully isolate several complex molecules. These molecules already contain the cannabinoid-like base structure and further processing of one such derivative led to a precursor of Δ⁹ -tetrahydrocannabinol. The most challenging step towards this precursor was an epoxidation step that was ultimately achieved via dimethyl dioxirane.

SUBMITTER: Hurrle T

PROVIDER: S-EPMC8121136 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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The Diels-Alder Approach towards Cannabinoid Derivatives and Formal Synthesis of Tetrahydrocannabinol (THC).

Hurrle Thomas T Gläser Franziska F Bröhmer Manuel C MC Nieger Martin M Bräse Stefan S

ChemistryOpen 20210501 5

Based on the Diels-Alder reaction of vinylchromenes with electron-poor dienophiles, we developed a strategy for the synthesis of tetrahydrocannabinol derivatives. Substituted vinyl chromenes could be converted with several dienophiles to successfully isolate several complex molecules. These molecules already contain the cannabinoid-like base structure and further processing of one such derivative led to a precursor of Δ<sup>9</sup> -tetrahydrocannabinol. The most challenging step towards this pr ...[more]

PMID: 33988908

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