The synthesis of hexahydro‐6H‐dibenzo[b,d]pyrans: Derivatives of 9‐Nor‐9β‐hydroxyhexahydrocannabinol

To assess the importance of the phenol functionality in cannabinoids for analgetic activity a new series of 9‐nor‐9β‐hydroxyhexahydrocannabinoids was prepared. The synthesis of 1‐substituted (H, CH2OH, OH, NH2) 6aβ,7,8,9,10,10aα‐hexahydro‐9β‐hydroxy‐6,6‐dimethyl‐3‐[1‐methyl‐4‐phenylbutoxy]‐6H‐dibenzo[b,d]pyrans from 3,5‐dihydroxystilbene, 3,3′,5,5′‐tetrahydroxystilbene or 1,3,5‐trihydroxybenzene is described. Relative stereochemistry and structure confirmations were obtained by nmr and X‐ray crystal analysis.