Synthesis of 5'-((2)H3)-(-)-11-Nor-9-carboxy-Δ9-Tetrahydrocannabinol Methyl Ester Methyl Ether

Article abstract of DOI:10.1016/S0040-4020(01)85608-8

A synthesis of 5'-((2)H3)-(-)-11-nor-carboxy-δ⁹-tetrahydrocannabinol methyl ester methyl ether (4) has been accomplished from α-bromoenone 10.The key steps are the stereocontrolled cyclobutane ring opening of the cuprate adduct 18 and the cyclization of the cyclohexenyl triflate 21 with excess iodotrimethylsilane to produce Δ⁹-cylohexenyl triflate 22.An efficient, stereospecific synthesis of optically active (-)-11-nor-9-keto-hexahydrocannabinol (8) has also been accomplished.