Total syntheses of cannabidiol and Δ1-tetrahydrocannabinol metabolites

Abstract

10-Hydroxycannabidiol [2-(10-hydroxy-p-mentha-1,8-dien-3-yl)-5-pentylresorcinol](Va), which has tentatively been identified as a cannabidiol metabolite, as well as 6α- and 6β-hydroxy-cannabidiol [(VIa) and (VIIa)], which are now reported to be metabolites, have been prepared from cannabidiol. Total syntheses of 7-hydroxycannabidiol triacetate (IIIb) and 7-acetoxy-Δ¹-tetrahydrocannabinol (9-acetoxymethyl-6a,7,8,10a-tetrahydro-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol)(IIc) from p-mentha-1,8-dien-7-ol are described.