Synthetic Strategies for Rare Cannabinoids Derived from Cannabis sativa - PubMed

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• PMID: 35648593
• DOI: 10.1021/acs.jnatprod.2c00155

Review

Synthetic Strategies for Rare Cannabinoids Derived from Cannabis sativa

Gia-Nam Nguyen et al. J Nat Prod. 2022.

Abstract

Efficient syntheses of eight key cannabinoids were established and optimized. Predominant cannabinoids such as cannabigerol (CBG-C₅) and cannabidiol (CBD-C₅) were prepared from olivetol via regioselective condensation. Further treatments of CBD led to Δ⁹-tetrahydrocannabinol (THC-C₅), Δ⁸-iso-tetrahydrocannabinol (iso-THC-C₅), and cannabinol (CBN-C₅). Alternatively, a [3 + 3] annulation between olivetol and citral yielded the minor cannabinoid cannabichromene (CBC-C₅), which was converted into two very rare polycycles, cannabicyclol (CBL-C₅) and cannabicitran (CBT-C₅), in a one-pot reaction. Finally, all eight syntheses were extended by utilizing resorcinol and two phenolic analogues, achieving a cannabinoid group with more than 30 compounds through a facile synthesis strategy.

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