posted on 2024-03-01, 21:31authored byAndrea Capucciati, Emanuele Casali, Arianna Bini, Filippo Doria, Daniele Merli, Alessio Porta
Cannabidiol (CBD), a prominent phytocannabinoid found
in various Cannabis chemotypes, is under extensive
investigation for
its therapeutic potential. Moreover, because it is nonpsychoactive,
it can also be utilized as a functional ingredient in foods and supplements
in certain countries, depending on its legal status. From a chemical
reactivity point of view, CBD can undergo conversion into different
structurally related compounds both during storage and after the consumption
of CBD-based products. The analytical determination of these compounds
is of paramount concern due to potential toxicity and the risk of
losing the active ingredient (CBD) title. Consequently, the complete
stereoselective total synthesis of representative CBD-derived compounds
has become a matter of great interest. The synthesis of pure CBD-derived
compounds, achievable in a few synthetic steps, is essential for preparing
analytical standards and facilitating biological studies. This paper
details the transformation of the readily available CBD into Δ8-THC, Δ9-THC, Δ8-iso-THC, CBE, HCDN, CBDQ, Δ6-iso-CBD, and 1,8-cineol cannabinoid (CCB). The described protocols were
executed without the extensive use of protecting groups, avoiding
tedious purifications, and ensuring complete control over the structural
features.