CONFORMATIONALLY RESTRICTED HYBRIDS OF CP-55,940 AND HHC - STEREOSELECTIVE SYNTHESIS AND ACTIVITY

A stereoselective total synthesis of each of the two diastereomeric C6 -hydroxyethyl analogs of (-)-9-nor-9 beta-hydroxyhexahydrocannabinol h as been reported. Control of the stereochemistry at C6 during the key step is accomplished through an intramolecular oxymercuration reaction . The prediction that the analogs would exhibit different degrees of b inding to the cannabinoid receptor was borne out. This observation she ds light on the stereochemical requirements of the receptor.