Fig. 1: Schemes of synthesis of enantiomer-CBD derivatives and final structures.
From: Carvone derived cannabidiol enantiomers as novel anticonvulsants
a Conversion of (+)-carvone into (-)-isopiperitenol in the synthesis of (+)-CBD. This process relies on the one-pot borane reduction / thermal rearrangement of an α,β-unsaturated hydrazone. b By uniting synthetic (+)-isopiperitenol with olivetol derivatives (Ar-H) under buffered Lewis acid conditions, we prepared a library of non-natural, enantiomer-CBD derivatives, each tailored with a different alkyl chain. While the derivatives with an odd number of alkyl carbons are known in their natural form, compounds featuring an even number of alkyl carbons have never been previously reported in either enantiomer form.
