Synthesis of 5′-(2H3)-(−)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol methyl ester methyl ether

Add time:08/12/2019    Source:sciencedirect.com

A synthesis of 5′-(2H3)-(−)-11-nor-9-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-cyclohexenyl triflate 22. An efficient, stereospecific synthesis of optically active (−)-d11-nor-9-keto-hexahydrocannabinol (8) has also been accomplished.

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