The title compound was obtained by methylation of phenol (I), which was prepared from pinene.
The cyclization of aldehyde (I) or verbenol (II) with resorcinol (III) by means of BF3 in dichloromethane gives the tetrahydrocannabiol analoge (IV) after column chromatography purification. Finally, this product is methylated by means of methyl iodide and K2CO3 in refluxing DMF.
Nabilone (I) was converted to the methylene analogue (II). Then, methylation of phenol group provided the title compound.
The cyclization of aldehyde (I) or verbenol (II) with resorcinol (III) by means of BF3 in dichloromethane gives the tetrahydrocannabiol analoge (IV) after column chromatography purification. The methylation of (IV) by means of methyl iodide and K2CO3 in refluxing DMF yields the methyl ether (V), which is treated with anhydrous ZnCl2 and HCl in chloroform affording the HCl adduct (VI). Finally, this compound is dehydrochlorinated to the target compound by means of potassium tricyclopentylcarbinolate (K-tcpc) in refluxing toluene.