Abstract
A synthesis of 5′-( 2H 3)-(−)-11-nor-9-carboxy-Δ 9-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 Δ 9-cyclohexenyl triflate 22. An efficient, stereospecific synthesis of optically active (−)-d11-nor-9-keto-hexahydrocannabinol ( 8) has also been accomplished.
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